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Search for "anticancer drugs" in Full Text gives 54 result(s) in Beilstein Journal of Organic Chemistry.
An overview of recent advances in duplex DNA recognition by small molecules
- Sayantan Bhaduri,
- Nihar Ranjan and
- Dev P. Arya
Beilstein J. Org. Chem. 2018, 14, 1051–1086, doi:10.3762/bjoc.14.93
- -rich sequences [41][42]. However, clinical development of TAM was discontinued due to severe myelotoxicity. With distamycin, netropsin and TAM as the lead compounds for novel anticancer drugs, a plethora of oligopyrrole derivatives were reported with the aim of increasing stability, greater DNA binding
Graphical Abstract
Figure 1: A figure showing the hydrogen bonding patterns observed in (a) duplex (b) triplex and (c) quadruple...
Figure 2: (a) Portions of MATα1–MATα2 are shown contacting the minor groove of the DNA substrate. Key arginin...
Figure 3: Chemical structures of naturally occurring and synthetic hybrid minor groove binders.
Figure 4: Synthetic structural analogs of distamycin A by replacing one or more pyrrole rings with other hete...
Figure 5: Pictorial representation of the binding model of pyrrole–imidazole (Py/Im) polyamides based on the ...
Figure 6: Chemical structures of synthetic “hairpin” pyrrole–imidazole (Py/Im) conjugates.
Figure 7: (a) Minor groove complex formation between DNA duplex and 8-ring cyclic Py/Im polyamide (conjugate ...
Figure 8: Telomere-targeting tandem hairpin Py/Im polyamides 23 and 24 capable of recognizing >10 base pairs; ...
Figure 9: Representative examples of recently developed DNA minor groove binders.
Figure 10: Chemical structures of bisbenzamidazoles Hoechst 33258 and 33342 and their synthetic structural ana...
Figure 11: Chemical structures of bisamidines such as diminazene, DAPI, pentamidine and their synthetic struct...
Figure 12: Representative examples of recently developed bisamidine derivatives.
Figure 13: Chemical structures of chromomycin, mithramycin and their synthetic structural analogs 91 and 92.
Figure 14: Chemical structures of well-known naturally occurring DNA binding intercalators.
Figure 15: Naturally occurring indolocarbazole rebeccamycin and its synthetic analogs.
Figure 16: Representative examples of naturally occurring and synthetic derivatives of DNA intercalating agent...
Figure 17: Several recent synthetic varieties of DNA intercalators.
Figure 18: Aminoglycoside (neomycin)–Hoechst 33258/intercalator conjugates.
Figure 19: Chemical structures of triazole linked neomycin dimers and neomycin–bisbenzimidazole conjugates.
Figure 20: Representative examples of naturally occurring and synthetic analogs of DNA binding alkylating agen...
Figure 21: Chemical structures of naturally occurring and synthetic analogs of pyrrolobenzodiazepines.
On the design principles of peptide–drug conjugates for targeted drug delivery to the malignant tumor site
- Eirinaios I. Vrettos,
- Gábor Mező and
- Andreas G. Tzakos
Beilstein J. Org. Chem. 2018, 14, 930–954, doi:10.3762/bjoc.14.80
- intervention, radiation and chemotherapy. Drugs used for this purpose are inevitably cytotoxic in order to eliminate cancer cells, but they lack selectivity that could be developed through targeting malignant cells (Figure 1). Due to the uncontrolled peripheral toxicity, anticancer drugs usually kill healthy
- anticancer drugs utilized to treat malignancies at the moment. Among this large pool of cytotoxic drugs, an array of them has been utilized as toxic warheads in PDCs and five representative examples are gemcitabine, doxorubicin, daunorubicin, paclitaxel and camptothecin (Figure 4). The main drawback of these
Graphical Abstract
Figure 1: Conventional chemotherapy versus targeted chemotherapy. Black color = Solid malignant tumor; red = ...
Figure 2: A. General structural architecture of the ideal navigated drug delivery system [31]. B. General structu...
Figure 3: Binding and penetration mechanism of iRGD. The iRGD peptide is accumulated on the surface of αv int...
Figure 4: Representative examples of anticancer drugs utilized for the construction of PDCs. The most usual c...
Figure 5: Illustration of the drug release mechanism from the self-immolative spacer PABC conjugated to a tum...
Figure 6: Structures of the PDCs named AN-152 and AN-207.
Figure 7: Structure of the PDC named AN-238.
Figure 8: Chemical structure and synthetic scheme for the PDC ANG1005. (A) ANG1005 is composed of three molec...
Figure 9: Structure of oxime linked Dau–GnRH-III conjugate with or without cathepsin B labile spacer and thei...
Figure 10: Synthesis of the most effective GnRH-III–Dau conjugate with two drug molecules [153].
Figure 11: Structures of the four different PDCs of D-Lys6-GnRH-I and gemcitabine (GSG, GSG2, 3G, 3G2) [19].
Figure 12: Structures of (A) native sunitinib; (B) SAN1 analog of sunitinib and (C) assembled PDC named SAN1GS...
Figure 13: Synthetic scheme for the formation of GSG and the unexpected side product [156].
Figure 14: Illustration of uncharted guanidinium peptide coupling reagent side reactions during PDCs synthesis ...
Figure 15: Putative mechanism for the formation of the uronium side product [156].
Development of novel cyclic NGR peptide–daunomycin conjugates with dual targeting property
- Andrea Angelo Pierluigi Tripodi,
- Szilárd Tóth,
- Kata Nóra Enyedi,
- Gitta Schlosser,
- Gergely Szakács and
- Gábor Mező
Beilstein J. Org. Chem. 2018, 14, 911–918, doi:10.3762/bjoc.14.78
- release; NGR peptides; oxime-linkage; targeted drug delivery; Introduction Targeted chemotherapy is one of the most promising approaches for selective cancer treatment that may decrease the toxic side effects of anticancer drugs. This therapeutic approach is based on the fact that tumor specific
- homing devices may provide dual targeted delivery of anticancer drugs. According to literature data, one of the most stable and tumor-selective cyclic NGR-peptides is c[KNGRE]-NH2, in which the α-amino group of the N-terminal Lys is coupled to the γ-carboxyl group of the glutamic acid residue (head-to
Graphical Abstract
Figure 1: Schematic synthesis of cyclic KNGRE (A) and XNGRE (B) drug conjugates. a) Mtt-cleavage: 2% TFA/DCM;...
Figure 2: (A) HT1080 and (B) HT-29 cells. Uptake of conjugate 1 (light green); 2 (red); 3 (light blue); 4 (pi...
Synthesis and in vitro biochemical evaluation of oxime bond-linked daunorubicin–GnRH-III conjugates developed for targeted drug delivery
- Sabine Schuster,
- Beáta Biri-Kovács,
- Bálint Szeder,
- Viktor Farkas,
- László Buday,
- Zsuzsanna Szabó,
- Gábor Halmos and
- Gábor Mező
Beilstein J. Org. Chem. 2018, 14, 756–771, doi:10.3762/bjoc.14.64
- Debrecen, 4032 Debrecen, Hungary 10.3762/bjoc.14.64 Abstract Gonadotropin releasing hormone-III (GnRH-III), a native isoform of the human GnRH isolated from sea lamprey, specifically binds to GnRH receptors on cancer cells enabling its application as targeting moieties for anticancer drugs. Recently, we
- (Dox), daunorubicin (Dau) or epirubicin are frequently used anticancer drugs. Their mode of action is based on a planar ring system which is important for intercalation into DNA [10]. In this way, anthracyclines can affect a broad range of DNA processes leading to an inhibited synthesis of
Graphical Abstract
Scheme 1: Syntheses of GnRH-III–[(4Lys(Bu)/4Ser, 6Aaa, 8Lys(Dau=Aoa)] bioconjugates. a) (1) 2% hydrazine in D...
Figure 1: Far-UV ECD spectra of GnRH-III and its drug conjugates in water (GnRH-III solid, K1 dash, K2 dot, 1...
Figure 2: Degradation of the GnRH-III bioconjugates by rat liver lysosomal homogenate. A) Cleavage sites prod...
Figure 3: Cytostatic effect of the GnRH-III bioconjugates at different concentrations on A) HT-29 and B) MCF-...
Figure 4: Cellular uptake of the GnRH-III bioconjugates at different concentrations on A) HT-29 and B) MCF-7 ...
Figure 5: Cellular uptake of bioconjugate K2 (40 µM) visualized by confocal laser scanning microscopy (CLSM) ...
Figure 6: Competitive inhibition of the GnRH-R on MCF-7 cells. Cellular uptake of the GnRH-III bioconjugate K2...
Vinylphosphonium and 2-aminovinylphosphonium salts – preparation and applications in organic synthesis
- Anna Kuźnik,
- Roman Mazurkiewicz and
- Beata Fryczkowska
Beilstein J. Org. Chem. 2017, 13, 2710–2738, doi:10.3762/bjoc.13.269
- anticancer drugs, antioxidants, or functional probes into the mitochondria [5][6][7][8]. Review 1. Synthesis of vinylphosphonium salts 1.1. Alkylation of phosphines with alkyl halides One of the most common methods for the preparation of vinylphosphonium salts 1 is the quaternization of vinylphosphines with
Graphical Abstract
Scheme 1: Generation of phosphorus ylides from vinylphosphonium salts.
Scheme 2: Intramolecular Wittig reaction with the use of vinylphosphonium salts.
Scheme 3: Alkylation of diphenylvinylphosphine with methyl or benzyl iodide.
Scheme 4: Methylation of isopropenyldiphenylphosphine with methyl iodide.
Scheme 5: Alkylation of phosphines with allyl halide derivatives and subsequent isomerization of intermediate...
Scheme 6: Alkylation of triphenylphosphine with vinyl triflates in the presence of (Ph3P)4Pd.
Scheme 7: Mechanism of alkylation of triphenylphosphine with vinyl triflates in the presence of (Ph3P)4Pd as ...
Scheme 8: β-Elimination of phenol from β-phenoxyethyltriphenylphosphonium bromide.
Scheme 9: β-Elimination of phenol from β-phenoxyethylphosphonium salts in an alkaline environment.
Scheme 10: Synthesis and subsequent dehydrohalogenation of α-bromoethylphosphonium bromide.
Scheme 11: Synthesis of tributylvinylphosphonium iodides via Peterson-type olefination of α-trimethylsilylphos...
Scheme 12: Synthesis of 1-cycloalkenetriphenylphosphonium salts by electrochemical oxidation of triphenylphosp...
Scheme 13: Suggested mechanism for the electrochemical synthesis of 1-cycloalkenetriphenylphosphonium salts.
Scheme 14: Generation of α,β-(dialkoxycarbonyl)vinylphosphonium salts by addition of triphenylphosphine to ace...
Scheme 15: Synthesis of 2-(N-acylamino)vinylphosphonium halides by imidoylation of β-carbonyl ylides with imid...
Scheme 16: Imidoylation of β-carbonyl ylides with imidoyl halides generated in situ.
Scheme 17: Synthesis of 2-benzoyloxyvinylphosphonium bromide from 2-propynyltriphenylphosphonium bromide.
Scheme 18: Synthesis of 2-aminovinylphosphonium salts via nucleophilic addition of amines to 2-propynyltriphen...
Scheme 19: Deacylation of 2-(N-acylamino)vinylphosphonium chlorides to 2-aminovinylphosphonium salts.
Scheme 20: Resonance structures of 2-aminovinylphosphonium salts and tautomeric equilibrium between aminovinyl...
Scheme 21: Synthesis of 2-aminovinylphosphonium salts by reaction of (formylmethyl)triphenylphosphonium chlori...
Scheme 22: Generation of ylides by reaction of vinyltriphenylphosphonium bromide with nucleophiles and their s...
Scheme 23: Intermolecular Wittig reaction with the use of vinylphosphonium bromide and organocopper compounds ...
Scheme 24: Intermolecular Wittig reaction with the use of ylides generated from vinylphosphonium bromides and ...
Scheme 25: Direct transformation of vinylphosphonium salts into ylides in the presence of potassium tert-butox...
Scheme 26: A general method for synthesis of carbo- and heterocyclic systems by the intramolecular Wittig reac...
Scheme 27: Synthesis of 2H-chromene by reaction of vinyltriphenylphosphonium bromide with sodium 2-formylpheno...
Scheme 28: Synthesis of 2,5-dihydro-2,3-dimethylfuran by reaction of vinylphosphonium bromide with 3-hydroxy-2...
Scheme 29: Synthesis of 2H-chromene and 2,5-dihydrofuran derivatives in the intramolecular Wittig reaction wit...
Scheme 30: Enantioselective synthesis of 3,6-dihydropyran derivatives from vinylphosphonium bromide and enanti...
Scheme 31: Synthesis of 2,5-dihydrothiophene derivatives in the intramolecular Wittig reaction from vinylphosp...
Scheme 32: Synthesis of bicyclic pyrrole derivatives in the reaction of vinylphosphonium halides and 2-pyrrolo...
Scheme 33: Stereoselective synthesis of bicyclic 2-pyrrolidinone derivatives in the reaction of vinylphosphoni...
Scheme 34: Stereoselective synthesis of 3-pyrroline derivatives in the intramolecular Wittig reaction from vin...
Scheme 35: Synthesis of cyclic alkenes in the intramolecular Wittig reaction from vinylphosphonium bromide and...
Scheme 36: Synthesis of 1,3-cyclohexadienes by reaction of 1,3-butadienyltriphenylphosphonium bromide with eno...
Scheme 37: Synthesis of bicyclo[3.3.0]octenes by reaction of vinylphosphonium salts with cyclic diketoester.
Scheme 38: Synthesis of quinoline derivatives in the intramolecular Wittig reaction from 2-(2-acylphenylamino)...
Scheme 39: Stereoselective synthesis of γ-aminobutyric acid in the intermolecular Wittig reaction from chiral ...
Scheme 40: Synthesis of allylamines in the intermolecular Wittig reaction from 2-aminovinylphosphonium bromide...
Scheme 41: A general route towards α,β-di(alkoxycarbonyl)vinylphosphonium salts and their subsequent possible ...
Scheme 42: Generation of resonance-stabilized phosphorus ylides via the reaction of triphenylphosphine with di...
Scheme 43: Synthesis of resonance-stabilized phosphorus ylides in the reaction of triphenylphosphine, dialkyl ...
Scheme 44: Synthesis of resonance-stabilized phosphorus ylides via the reaction of triphenylphosphine with dia...
Scheme 45: Generation of resonance-stabilized phosphorus ylides in the reaction of acetylenedicarboxylate, tri...
Scheme 46: Synthesis of resonance-stabilized phosphorus ylides via the reaction of dialkyl acetylenedicarboxyl...
Scheme 47: Synthesis of resonance-stabilized ylides derived from semicarbazones, aromatic amides, and 3-(aryls...
Scheme 48: Synthesis of resonance-stabilized ylides via the reaction of triphenylphosphine with dialkyl acetyl...
Scheme 49: Synthesis of resonance-stabilized ylides in the reaction of triphenylphosphine, dialkyl acetylenedi...
Scheme 50: Synthesis of N-acylated α,β-unsaturated γ-lactams via resonance-stabilized phosphorus ylides derive...
Scheme 51: Synthesis of resonance-stabilized phosphorus ylides derived from 6-amino-N,N'-dimethyluracil and th...
Scheme 52: Generation of resonance-stabilized phosphorus ylides in the reaction of triphenylphosphine, dialkyl...
Scheme 53: Synthesis of resonance-stabilized phosphorus ylides via the reaction of triphenylphosphine with dia...
Scheme 54: Synthesis of 1,3-dienes via intramolecular Wittig reaction with the use of resonance-stabilized yli...
Scheme 55: Synthesis of 1,3-dienes in the intramolecular Wittig reaction from ylides generated from dimethyl a...
Scheme 56: Synthesis of 4-(2-quinolyl)cyclobutene-1,2,3-tricarboxylic acid triesters and isomeric cyclopenteno...
Scheme 57: Synthesis of 4-arylquinolines via resonance-stabilized ylides in the intramolecular Wittig reaction....
Scheme 58: Synthesis of furan derivatives via resonance-stabilized ylides in the intramolecular Wittig reactio...
Scheme 59: Synthesis of 1,3-indanedione derivatives via resonance-stabilized ylides in the intermolecular Witt...
Scheme 60: Synthesis of coumarin derivatives via nucleophilic displacement of the triphenylphosphonium group i...
Scheme 61: Synthesis of 6-formylcoumarin derivatives and their application in the synthesis of dyads.
Scheme 62: Synthesis of di- and tricyclic coumarin derivatives in the reaction of pyrocatechol with two vinylp...
Scheme 63: Synthesis of mono-, di-, and tricyclic derivatives in the reaction of pyrogallol with one or two vi...
Scheme 64: Synthesis of 1,4-benzoxazine derivative by nucleophilic displacement of the triphenylphosphonium gr...
Scheme 65: Synthesis of 7-oxo-7H-pyrido[1,2,3-cd]perimidine derivative via nucleophilic displacement of the tr...
Scheme 66: Application of vinylphosphonium salts in the Diels–Alder reaction with dienes.
Scheme 67: Synthesis of pyrroline derivatives from vinylphosphonium bromide and 5-(4H)-oxazolones.
Scheme 68: Synthesis of pyrrole derivatives in the reactions of vinyltriphenylphosphonium bromide with protona...
Scheme 69: Synthesis of dialkyl 2-(alkylamino)-5-aryl-3,4-furanedicarboxylates via intermediate α,β-di(alkoxyc...
Scheme 70: Synthesis of 1,4-benzoxazine derivatives from acetylenedicarboxylates, phosphines, and 1-nitroso-2-...
Exploring mechanochemistry to turn organic bio-relevant molecules into metal-organic frameworks: a short review
- Vânia André,
- Sílvia Quaresma,
- João Luís Ferreira da Silva and
- M. Teresa Duarte
Beilstein J. Org. Chem. 2017, 13, 2416–2427, doi:10.3762/bjoc.13.239
- enhancement of MOF structural and stability properties [90][91]. Bioactive molecules like caffeine [92][93] and anticancer drugs [94][95][96][97][98] were incorporated in ZIF-8 and tests proved that these systems allowed for a controlled drug release. Further studies involving ZIF-8 with encapsulated
- anticancer drugs have also shown that these have potential to be used in fluorescence imaging. The number of reports on MOFs synthesized by mechanochemistry [8][28][50][99][100][101] has been increasing and some in situ studies on the mechanosynthesis of MOFs and coordination polymers are already being
Graphical Abstract
Figure 1: a) Detailed supramolecular packing of a gabapentin–Er network; b) view along the b-axis of the supr...
Figure 2: a) Mechanochemical reactivity between the excipient MgO and carboxylic acid NSAID molecules; b) NSA...
Figure 3: Mechanochemical reaction to form Cu3(BTC)2 and the structure of Cu3(BTC)2·(HKUST-1) as reported by ...
Figure 4: Mechanochemical syntheses of coordination polymers from ZnO and fumaric acid. Reprinted with permis...
Figure 5: Mechanochemical synthesis of pillared MOFs from ZnO, fumaric acid and two auxiliary ligands (bipy a...
Figure 6: a) Synthesis of ZIF-8; b) fragment of the crystal structure of ZIF-8. Reprinted with permission fro...
Figure 7: a) Mechanochemical reaction of salicylic acid with Bi2O3 yielding bismuth mono-, di- and trisalicyl...
Total syntheses of the archazolids: an emerging class of novel anticancer drugs
- Stephan Scheeff and
- Dirk Menche
Beilstein J. Org. Chem. 2017, 13, 1085–1098, doi:10.3762/bjoc.13.108
Graphical Abstract
Scheme 1: Molecular structures of the archazolids.
Scheme 2: Retrosynthetic analysis of archazolid A by the Menche group.
Scheme 3: Synthesis of north-eastern fragment 5 through a Paterson anti-aldol addition and multiple Still–Gen...
Scheme 4: Synthesis of 4 through an Abiko–Masamune anti-aldol addition.
Scheme 5: Thiazol construction and synthesis of the southern fragment 6.
Scheme 6: Completion of the total synthesis of archazolid A.
Scheme 7: Synthesis of archazolid B (2) by a ring closing Heck reaction of 38.
Scheme 8: Retrosynthetic analysis of archazolid B by the Trauner group.
Scheme 9: Synthesis of acid 40 from Roche ester 41 involving a highly efficient Trost–Alder ene reaction.
Scheme 10: Synthesis of precursor 39 for the projected relay RCM reaction.
Scheme 11: Final steps of Trauner’s total synthesis of archazolid B.
Scheme 12: Overview of the different retrosynthetic approaches for the synthesis of dihydroarchazolid B (3) re...
Scheme 13: Fragment synthesis of 69 towards the total synthesis of 3.
Scheme 14: Organometallic addition of the side chain to access free alcohol 75.
Glyco-gold nanoparticles: synthesis and applications
- Federica Compostella,
- Olimpia Pitirollo,
- Alessandro Silvestri and
- Laura Polito
Beilstein J. Org. Chem. 2017, 13, 1008–1021, doi:10.3762/bjoc.13.100
- metal-based anticancer drugs need to be developed. Recently, it has been reported the interesting synthesis of AuNPs coated with glyco-polymers and functionalized with gold(I) triphenylphosphine (Figure 7) [88]. This work showed the potentiality of these structures as novel cancer therapeutic drugs. The
Graphical Abstract
Figure 1: Schematic overview on the glyco-gold nanoparticles synthetic approaches.
Figure 2: Glyco-gold nanoparticles: metallic core and glyco-coating contribute to the production of the versa...
Figure 3: The protein–carbohydrate interactions analyzed by conventional dark field microscopy. The interacti...
Figure 4: Copper-free cycloaddition (SPAAC) of azido galactoside on cyclooctyne and schematic depiction of Au...
Figure 5: A photoaffinity labeling (PAL) approach based on glyco-gold nanoparticles is able to recognize and ...
Figure 6: Design of the fiber-type “Sugar Chips”. AuNPs are firstly immobilized on an optical fiber functiona...
Figure 7: Design of GAuNPs, displaying both sugar residues and the anticancer Au(I)PPh3. Reprinted with permi...
Synthesis of 1-indanones with a broad range of biological activity
- Marika Turek,
- Dorota Szczęsna,
- Marek Koprowski and
- Piotr Bałczewski
Beilstein J. Org. Chem. 2017, 13, 451–494, doi:10.3762/bjoc.13.48
- as antiviral and antibacterial agents [5] (I and II), anticancer drugs [6] (VI), pharmaceuticals used in the Alzheimer’s disease treatment [7] (III), cardiovascular drugs [7] (IV), insecticides, fungicides, herbicides [8] (V) and non-nucleoside, low molecular drugs for the hepatitis C treatment
Graphical Abstract
Figure 1: Biologically active 1-indanones and their structural analogues.
Figure 2: Number of papers about (a) 1-indanones, (b) synthesis of 1-indanones.
Scheme 1: Synthesis of 1-indanone (2) from hydrocinnamic acid (1).
Scheme 2: Synthesis of 1-indanone (2) from 3-(2-bromophenyl)propionic acid (3).
Scheme 3: Synthesis of 1-indanones 5 from 3-arylpropionic acids 4.
Scheme 4: Synthesis of kinamycin (9a) and methylkinamycin C (9b).
Scheme 5: Synthesis of trifluoromethyl-substituted arylpropionic acids 12, 1-indanones 13 and dihydrocoumarin...
Scheme 6: Synthesis of 1-indanones 16 from benzoic acids 15.
Scheme 7: Synthesis of 1-indanones 18 from arylpropionic and 3-arylacrylic acids 17.
Scheme 8: The NbCl5-induced one-step synthesis of 1-indanones 22.
Scheme 9: Synthesis of biologically active 1-indanone derivatives 26.
Scheme 10: Synthesis of enantiomerically pure indatraline ((−)-29).
Scheme 11: Synthesis of 1-indanone (2) from the acyl chloride 30.
Scheme 12: Synthesis of the mechanism-based inhibitors 33 of coelenterazine.
Scheme 13: Synthesis of the indane 2-imidazole derivative 37.
Scheme 14: Synthesis of fluorinated PAHs 41.
Scheme 15: Synthesis of 1-indanones 43 via transition metal complexes-catalyzed carbonylative cyclization of m...
Scheme 16: Synthesis of 6-methyl-1-indanone (46).
Scheme 17: Synthesis of 1-indanone (2) from ester 48.
Scheme 18: Synthesis of benzopyronaphthoquinone 51 from the spiro-1-indanone 50.
Scheme 19: Synthesis of the selective endothelin A receptor antagonist 55.
Scheme 20: Synthesis of 1-indanones 60 from methyl vinyl ketone (57).
Scheme 21: Synthesis of 1-indanones 64 from diethyl phthalate 61.
Scheme 22: Synthesis of 1-indanone derivatives 66 from various Meldrum’s acids 65.
Scheme 23: Synthesis of halo 1-indanones 69.
Scheme 24: Synthesis of substituted 1-indanones 71.
Scheme 25: Synthesis of spiro- and fused 1-indanones 73 and 74.
Scheme 26: Synthesis of spiro-1,3-indanodiones 77.
Scheme 27: Mechanistic pathway for the NHC-catalyzed Stetter–Aldol–Michael reaction.
Scheme 28: Synthesis of 2-benzylidene-1-indanone derivatives 88a–d.
Scheme 29: Synthesis of 1-indanone derivatives 90a–i.
Scheme 30: Synthesis of 1-indanones 96 from o-bromobenzaldehydes 93 and alkynes 94.
Scheme 31: Synthesis of 3-hydroxy-1-indanones 99.
Scheme 32: Photochemical preparation of 1-indanones 103 from ketones 100.
Scheme 33: Synthesis of chiral 3-aryl-1-indanones 107.
Scheme 34: Photochemical isomerization of 2-methylbenzil 108.
Scheme 35: Synthesis of 2-hydroxy-1-indanones 111a–c.
Scheme 36: Synthesis of 1-indanone derivatives 113 and 114 from η6-1,2-dioxobenzocyclobutene complex 112.
Scheme 37: Synthesis of nakiterpiosin (117).
Scheme 38: Synthesis of 2-alkyl-1-indanones 120.
Scheme 39: Synthesis of fluorine-containing 1-indanone derivatives 123.
Scheme 40: Synthesis of 2-benzylidene and 2-benzyl-1-indanones 126, 127 from the chalcone 124.
Scheme 41: Synthesis of 2-bromo-6-methoxy-3-phenyl-1-indanone (130).
Scheme 42: Synthesis of combretastatin A-4-like indanones 132a–s.
Figure 3: Chemical structures of investigated dienones 133 and synthesized cyclic products 134–137.
Figure 4: Chemical structures of 1-indanones and their heteroatom analogues 138–142.
Scheme 43: Synthesis of 2-phosphorylated and 2-non-phosphorylated 1-indanones 147 and 148 from β-ketophosphona...
Scheme 44: Photochemical synthesis of 1-indanone derivatives 150, 153a, 153b.
Scheme 45: Synthesis of polysubstituted-1-indanones 155, 157.
Scheme 46: Synthesis of 1-indanones 159a–g from α-arylpropargyl alcohols 158 using RhCl(PPh3)3 as a catalyst.
Scheme 47: Synthesis of optically active 1-indanones 162 via the asymmetric Rh-catalyzed isomerization of race...
Scheme 48: Mechanism of the Rh-catalyzed isomerization of α-arylpropargyl alcohols 161 to 1-indanones 162.
Figure 5: Chemical structure of abicoviromycin (168) and its new benzo derivative 169.
Scheme 49: Synthesis of racemic benzoabicoviromycin 172.
Scheme 50: Synthesis of [14C]indene 176.
Scheme 51: Synthesis of indanone derivatives 178–180.
Scheme 52: Synthesis of racemic pterosin A 186.
Scheme 53: Synthesis of trans-2,3-disubstituted 1-indanones 189.
Scheme 54: Synthesis of 3-aryl-1-indanone derivatives 192.
Scheme 55: Synthesis of 1-indanone derivatives 194 from 3-(2-iodoaryl)propanonitriles 193.
Scheme 56: Synthesis of 1-indanones 200–204 by cyclization of aromatic nitriles.
Scheme 57: Synthesis of 1,1’-spirobi[indan-3,3’-dione] derivative 208.
Scheme 58: Total synthesis of atipamezole analogues 211.
Scheme 59: Synthesis of 3-[4-(1-piperidinoethoxy)phenyl]spiro[indene-1,1’-indan]-5,5’-diol hydrochloride 216.
Scheme 60: Synthesis of 3-arylindan-1-ones 219.
Scheme 61: Synthesis of 2-hydroxy-1-indanones 222.
Scheme 62: Synthesis of the 1-indanone 224 from the THP/MOM protected chalcone epoxide 223.
Scheme 63: Synthesis of 1-indanones 227 from γ,δ-epoxy ketones 226.
Scheme 64: Synthesis of 2-hydroxy-2-methylindanone (230).
Scheme 65: Synthesis of 1-indanone derivatives 234 from cyclopropanol derivatives 233.
Scheme 66: Synthesis of substituted 1-indanone derivatives 237.
Scheme 67: Synthesis of 7-methyl substituted 1-indanone 241 from 1,3-pentadiene (238) and 2-cyclopentenone (239...
Scheme 68: Synthesis of disubstituted 1-indanone 246 from the siloxydiene 244 and 2-cyclopentenone 239.
Scheme 69: Synthesis of 5-hydroxy-1-indanone (250) via the Diels–Alder reaction of 1,3-diene 248 with sulfoxid...
Scheme 70: Synthesis of halogenated 1-indanones 253a and 253b.
Scheme 71: Synthesis of 1-indanones 257 and 258 from 2-bromocyclopentenones 254.
Scheme 72: Synthesis of 1-indanone 261 from 2-bromo-4-acetoxy-2-cyclopenten-1-one (260) and 1,2-dihydro-4-viny...
Scheme 73: Synthesis of 1-indanone 265 from 1,2-dihydro-7-methoxy-4-vinylnaphthalene (262) and bromo-substitut...
Scheme 74: Synthesis of 1-indanone 268 from dihydro-3-vinylphenanthrene 266 and 4-acetoxy-2-cyclopenten-1-one (...
Scheme 75: Synthesis of 1-indanone 271 from phenylselenyl-substituted cyclopentenone 268.
Scheme 76: Synthesis of 1-indanone 272 from the trienone 270.
Scheme 77: Synthesis of the 1-indanone 276 from the aldehyde 273.
Scheme 78: Synthesis of 1-indanones 278 and 279.
Scheme 79: Synthesis of 1-indanone 285 from octa-1,7-diyne (282) and cyclopentenone 239.
Scheme 80: Synthesis of benz[f]indan-1-one (287) from cyclopentenone 239 and o-bis(dibromomethyl)benzene (286)....
Scheme 81: Synthesis of 3-methyl-substituted benz[f]indan-1-one 291 from o-bis(dibromomethyl)benzene (286) and...
Scheme 82: Synthesis of benz[f]indan-1-one (295) from the anthracene epidioxide 292.
Scheme 83: Synthesis of 1-indanone 299 from homophthalic anhydride 298 and cyclopentynone 297.
Scheme 84: Synthesis of cyano-substituted 1-indanone derivative 301 from 2-cyanomethylbenzaldehyde (300) and c...
Scheme 85: Synthesis of 1-indanone derivatives 303–305 from ketene dithioacetals 302.
Scheme 86: Synthesis of 1-indanones 309–316.
Scheme 87: Mechanism of the hexadehydro-Diels–Alder (HDDA) reaction.
Scheme 88: Synthesis of 1-indenone 318 and 1-indanones 320 and 321 from tetraynes 317 and 319.
Scheme 89: Synthesis of 1-indanone 320 from the triyn 319.
Scheme 90: Synthesis 1-indanone 328 from 2-methylfuran 324.
Scheme 91: Synthesis of 1-indanones 330 and 331 from furans 329.
Scheme 92: Synthesis of 1-indanone 333 from the cycloadduct 332.
Scheme 93: Synthesis of (S)-3-arylindan-1-ones 335.
Scheme 94: Synthesis of (R)-2-acetoxy-1-indanone 338.
Figure 6: Chemical structures of obtained cyclopenta[α]phenanthrenes 339.
Scheme 95: Synthesis of the benzoindanone 343 from arylacetaldehyde 340 with 1-trimethylsilyloxycyclopentene (...
Rearrangements of organic peroxides and related processes
- Ivan A. Yaremenko,
- Vera A. Vil’,
- Dmitry V. Demchuk and
- Alexander O. Terent’ev
Beilstein J. Org. Chem. 2016, 12, 1647–1748, doi:10.3762/bjoc.12.162
- agents and initiators for free-radical reactions both in industry and in laboratory. These compounds are produced and involved in various natural and biological processes and were explored extensively as antimalarial agents, anthelmintics, and anticancer drugs. Organic peroxides, such as alkyl
Graphical Abstract
Figure 1: The named transformations considered in this review.
Scheme 1: The Baeyer–Villiger oxidation.
Scheme 2: The general mechanism of the peracid-promoted Baeyer–Villiger oxidation.
Scheme 3: General mechanism of the Lewis acid-catalyzed Baeyer–Villiger rearrangement.
Scheme 4: The theoretically studied mechanism of the BV oxidation reaction promoted by H2O2 and the Lewis aci...
Scheme 5: Proton movements in the transition states of the Baeyer–Villiger oxidation.
Scheme 6: The dependence of the course of the Baeyer–Villiger oxidation on the type of O–O-bond cleavage in t...
Scheme 7: The acid-catalyzed Baeyer–Villiger oxidation of cyclic epoxy ketones 22.
Scheme 8: Oxidation of isophorone oxide 29.
Scheme 9: Synthesis of acyl phosphate 32 from acyl phosphonate 31.
Scheme 10: Synthesis of aflatoxin B2 (36).
Scheme 11: The Baeyer–Villiger rearrangement of ketones 37 to lactones 38.
Scheme 12: Synthesis of 3,4-dimethoxybenzoic acid (40) via Baeyer–Villiger oxidation.
Scheme 13: Oxone transforms α,β-unsaturated ketones 43 into vinyl acetates 44.
Scheme 14: The Baeyer–Villiger oxidation of ketones 45 using diaryl diselenide and hydrogen peroxide.
Scheme 15: Baeyer–Villiger oxidation of (E)-2-methylenecyclobutanones.
Scheme 16: Oxidation of β-ionone (56) by H2O2/(BnSe)2 with formation of (E)-2-(2,6,6-trimethylcyclohex-1-en-1-...
Scheme 17: The mechanism of oxidation of ketones 58a–f by hydrogen peroxide in the presence of arsonated polys...
Scheme 18: Oxidation of ketone (58b) by H2O2 to 6-methylcaprolactone (59b) catalyzed by Pt complex 66·BF4.
Scheme 19: Oxidation of ketones 67 with H2O2 in the presence of [(dppb}Pt(µ-OH)]22+.
Scheme 20: The mechanism of oxidation of ketones 67 in the presence of [(dppb}Pt(µ-OH)]22+ and H2O2.
Scheme 21: Oxidation of benzaldehydes 69 in the presence of the H2O2/MeReO3 system.
Scheme 22: Oxidation of acetophenones 72 in the presence of the H2O2/MeReO3 system.
Scheme 23: Baeyer–Villiger oxidation of 2-adamantanone (45c) in the presence of Sn-containing mesoporous silic...
Scheme 24: Aerobic Baeyer–Villiger oxidation of ketones 76 using metal-free carbon.
Scheme 25: A regioselective Baeyer-Villiger oxidation of functionalized cyclohexenones 78 into a dihydrooxepin...
Scheme 26: The oxidation of aldehydes and ketones 80 by H2O2 catalyzed by Co4HP2Mo15V3O62.
Scheme 27: The cleavage of ketones 82 with hydrogen peroxide in alkaline solution.
Scheme 28: Oxidation of ketones 85 to esters 86 with H2O2–urea in the presence of KHCO3.
Scheme 29: Mechanism of the asymmetric oxidation of cyclopentane-1,2-dione 87a with the Ti(OiPr)4/(+)DET/t-BuO...
Scheme 30: The oxidation of cis-4-tert-butyl-2-fluorocyclohexanone (93) with m-chloroperbenzoic acid.
Scheme 31: The mechanism of the asymmetric oxidation of 3-substituted cyclobutanone 96a in the presence of chi...
Scheme 32: Enantioselective Baeyer–Villiger oxidation of cyclic ketones 98.
Scheme 33: Regio- and enantioselective Baeyer–Villiger oxidation of cyclic ketones 101.
Scheme 34: The proposed mechanism of the Baeyer–Villiger oxidation of acetal 105f.
Scheme 35: Synthesis of hydroxy-10H-acridin-9-one 117 from tetramethoxyanthracene 114.
Scheme 36: The Baeyer–Villiger oxidation of the fully substituted pyrrole 120.
Scheme 37: The Criegee rearrangement.
Scheme 38: The mechanism of the Criegee reaction of a peracid with a tertiary alcohol 122.
Scheme 39: Criegee rearrangement of decaline ethylperoxoate 127 into ketal 128.
Scheme 40: The ionic cleavage of 2-methoxy-2-propyl perester 129.
Scheme 41: The Criegee rearrangement of α-methoxy hydroperoxide 136.
Scheme 42: Synthesis of enol esters and acetals via the Criegee rearrangement.
Scheme 43: Proposed mechanism of the transformation of 1-hydroperoxy-2-oxabicycloalkanones 147a–d.
Scheme 44: Transformation of 3-hydroxy-1,2-dioxolanes 151 into diketone derivatives 152.
Scheme 45: Criegee rearrangement of peroxide 153 with the mono-, di-, and tri-O-insertion.
Scheme 46: The sequential Criegee rearrangements of adamantanes 157a,b.
Scheme 47: Synthesis of diaryl carbonates 160a–d from triarylmethanols 159a–d through successive oxygen insert...
Scheme 48: The synthesis of sesquiterpenes 162 from ketone 161 with a Criegee rearrangement as one key step.
Scheme 49: Synthesis of trans-hydrindan derivatives 164, 165.
Scheme 50: The Hock rearrangement.
Scheme 51: The general scheme of the cumene process.
Scheme 52: The Hock rearrangement of aliphatic hydroperoxides.
Scheme 53: The mechanism of solvolysis of brosylates 174a–c and spiro cyclopropyl carbinols 175a–c in THF/H2O2....
Scheme 54: The fragmentation mechanism of hydroperoxy acetals 178 to esters 179.
Scheme 55: The acid-catalyzed rearrangement of phenylcyclopentyl hydroperoxide 181.
Scheme 56: The peroxidation of tertiary alcohols in the presence of a catalytic amount of acid.
Scheme 57: The acid-catalyzed reaction of bicyclic secondary alcohols 192 with hydrogen peroxide.
Scheme 58: The photooxidation of 5,6-disubstituted 3,4-dihydro-2H-pyrans 196.
Scheme 59: The oxidation of tertiary alcohols 200a–g, 203a,b, and 206.
Scheme 60: Transformation of functional peroxide 209 leading to 2,3-disubstitued furans 210 in one step.
Scheme 61: The synthesis of carbazoles 213 via peroxide rearrangement.
Scheme 62: The construction of C–N bonds using the Hock rearrangement.
Scheme 63: The synthesis of moiety 218 from 217 which is a structural motif in the antitumor–antibiotic of CC-...
Scheme 64: The in vivo oxidation steps of cholesterol (219) by singlet oxygen.
Scheme 65: The proposed mechanism of the rearrangement of cholesterol-5α-OOH 220.
Scheme 66: Photochemical route to artemisinin via Hock rearrangement of 223.
Scheme 67: The Kornblum–DeLaMare rearrangement.
Scheme 68: Kornblum–DeLaMare transformation of 1-phenylethyl tert-butyl peroxide (225).
Scheme 69: The synthesis 4-hydroxyenones 230 from peroxide 229.
Scheme 70: The Kornblum–DeLaMare rearrangement of peroxide 232.
Scheme 71: The reduction of peroxide 234.
Scheme 72: The Kornblum–DeLaMare rearrangement of endoperoxide 236.
Scheme 73: The rearrangement of peroxide 238 under Kornblum–DeLaMare conditions.
Scheme 74: The proposed mechanism of rearrangement of peroxide 238.
Scheme 75: The Kornblum–DeLaMare rearrangement of peroxides 242a,b.
Scheme 76: The base-catalyzed rearrangements of bicyclic endoperoxides having electron-withdrawing substituent...
Scheme 77: The base-catalyzed rearrangements of bicyclic endoperoxides 249a,b having electron-donating substit...
Scheme 78: The base-catalyzed rearrangements of bridge-head substituted bicyclic endoperoxides 251a,b.
Scheme 79: The Kornblum–DeLaMare rearrangement of hydroperoxide 253.
Scheme 80: Synthesis of β-hydroxy hydroperoxide 254 from endoperoxide 253.
Scheme 81: The amine-catalyzed rearrangement of bicyclic endoperoxide 263.
Scheme 82: The base-catalyzed rearrangement of meso-endoperoxide 268 into 269.
Scheme 83: The photooxidation of 271 and subsequent Kornblum–DeLaMare reaction.
Scheme 84: The Kornblum–DeLaMare rearrangement as one step in the oxidation reaction of enamines.
Scheme 85: The Kornblum–DeLaMare rearrangement of 3,5-dihydro-1,2-dioxenes 284, 1,2-dioxanes 286, and tert-but...
Scheme 86: The Kornblum–DeLaMare rearrangement of epoxy dioxanes 290a–d.
Scheme 87: Rearrangement of prostaglandin H2 292.
Scheme 88: The synthesis of epicoccin G (297).
Scheme 89: The Kornblum–DeLaMare rearrangement used in the synthesis of phomactin A.
Scheme 90: The Kornblum–DeLaMare rearrangement in the synthesis of 3H-quinazolin-4-one 303.
Scheme 91: The Kornblum–DeLaMare rearrangement in the synthesis of dolabriferol (308).
Scheme 92: Sequential transformation of 3-substituted 2-pyridones 309 into 3-hydroxypyridine-2,6-diones 311 in...
Scheme 93: The Kornblum–DeLaMare rearrangement of peroxide 312 into hydroxy enone 313.
Scheme 94: The Kornblum–DeLaMare rearrangement in the synthesis of polyfunctionalized carbonyl compounds 317.
Scheme 95: The Kornblum–DeLaMare rearrangement in the synthesis of (Z)-β-perfluoroalkylenaminones 320.
Scheme 96: The Kornblum–DeLaMare rearrangement in the synthesis of γ-ketoester 322.
Scheme 97: The Kornblum–DeLaMare rearrangement in the synthesis of diterpenoids 326 and 328.
Scheme 98: The synthesis of natural products hainanolidol (331) and harringtonolide (332) from peroxide 329.
Scheme 99: The synthesis of trans-fused butyrolactones 339 and 340.
Scheme 100: The synthesis of leucosceptroid C (343) and leucosceptroid P (344) via the Kornblum–DeLaMare rearra...
Scheme 101: The Dakin oxidation of arylaldehydes or acetophenones.
Scheme 102: The mechanism of the Dakin oxidation.
Scheme 103: A solvent-free Dakin reaction of aromatic aldehydes 356.
Scheme 104: The organocatalytic Dakin oxidation of electron-rich arylaldehydes 358.
Scheme 105: The Dakin oxidation of electron-rich arylaldehydes 361.
Scheme 106: The Dakin oxidation of arylaldehydes 358 in water extract of banana (WEB).
Scheme 107: A one-pot approach towards indolo[2,1-b]quinazolines 364 from indole-3-carbaldehydes 363 through th...
Scheme 108: The synthesis of phenols 367a–c from benzaldehydes 366a-c via acid-catalyzed Dakin oxidation.
Scheme 109: Possible transformation paths of the highly polarized boric acid coordinated H2O2–aldehyde adduct 3...
Scheme 110: The Elbs oxidation of phenols 375 to hydroquinones.
Scheme 111: The mechanism of the Elbs persulfate oxidation of phenols 375 affording p-hydroquinones 376.
Scheme 112: Oxidation of 2-pyridones 380 under Elbs persulfate oxidation conditions.
Scheme 113: Synthesis of 3-hydroxy-4-pyridone (384) via an Elbs oxidation of 4-pyridone (382).
Scheme 114: The Schenck rearrangement.
Scheme 115: The Smith rearrangement.
Scheme 116: Three main pathways of the Schenck rearrangement.
Scheme 117: The isomerization of hydroperoxides 388 and 389.
Scheme 118: Trapping of dioxacyclopentyl radical 392 by oxygen.
Scheme 119: The hypothetical mechanism of the Schenck rearrangement of peroxide 394.
Scheme 120: The autoxidation of oleic acid (397) with the use of labeled isotope 18O2.
Scheme 121: The rearrangement of 18O-labeled hydroperoxide 400 under an atmosphere of 16O2.
Scheme 122: The rearrangement of the oleate-derived allylic hydroperoxides (S)-421 and (R)-425.
Scheme 123: Mechanisms of Schenck and Smith rearrangements.
Scheme 124: The rearrangement and cyclization of 433.
Scheme 125: The Wieland rearrangement.
Scheme 126: The rearrangement of bis(triphenylsilyl) 439 or bis(triphenylgermyl) 441 peroxides.
Scheme 127: The oxidative transformation of cyclic ketones.
Scheme 128: The hydroxylation of cyclohexene (447) in the presence of tungstic acid.
Scheme 129: The oxidation of cyclohexene (447) under the action of hydrogen peroxide.
Scheme 130: The reaction of butenylacetylacetone 455 with hydrogen peroxide.
Scheme 131: The oxidation of bridged 1,2,4,5-tetraoxanes.
Scheme 132: The proposed mechanism for the oxidation of bridged 1,2,4,5-tetraoxanes.
Scheme 133: The rearrangement of ozonides.
Scheme 134: The acid-catalyzed oxidative rearrangement of malondialdehydes 462 under the action of H2O2.
Scheme 135: Pathways of the Lewis acid-catalyzed cleavage of dialkyl peroxides 465 and ozonides 466.
Scheme 136: The mechanism of the transformation of (tert-butyldioxy)cyclohexanedienones 472.
Scheme 137: The synthesis of Vitamin K3 from 472a.
Scheme 138: Proposed mechanism for the transformation of 478d into silylated endoperoxide 479d.
Scheme 139: The rearrangement of hydroperoxide 485 to form diketone 486.
Scheme 140: The base-catalyzed rearrangement of cyclic peroxides 488a–g.
Scheme 141: Synthesis of chiral epoxides and aldols from peroxy hemiketals 491.
Scheme 142: The multistep transformation of (R)-carvone (494) to endoperoxides 496a–e.
Scheme 143: The decomposition of anthracene endoperoxide 499.
Scheme 144: Synthesis of esters 503 from aldehydes 501 via rearrangement of peroxides 502.
Scheme 145: Two possible paths for the base-promoted decomposition of α-azidoperoxides 502.
Scheme 146: The Story decomposition of cyclic diperoxide 506a.
Scheme 147: The Story decomposition of cyclic triperoxide 506b.
Scheme 148: The thermal rearrangement of endoperoxides A into diepoxides B.
Scheme 149: The transformation of peroxide 510 in the synthesis of stemolide (511).
Scheme 150: The possible mechanism of the rearrangement of endoperoxide 261g.
Scheme 151: The photooxidation of indene 517.
Scheme 152: The isomerization of ascaridole (523).
Scheme 153: The isomerization of peroxide 525.
Scheme 154: The thermal transformation of endoperoxide 355.
Scheme 155: The photooxidation of cyclopentadiene (529) at a temperature higher than 0 °C.
Scheme 156: The thermal rearrangement of endoperoxides 538a,b.
Scheme 157: The transformation of peroxides 541.
Scheme 158: The thermal rearrangements of strained cyclic peroxides.
Scheme 159: The thermal rearrangement of diacyl peroxide 551 in the synthesis of C4-epi-lomaiviticin B core 553....
Scheme 160: The 1O2 oxidation of tryptophan (554) and rearrangement of dioxetane intermediate 555.
Scheme 161: The Fe(II)-promoted cleavage of aryl-substituted bicyclic peroxides.
Scheme 162: The proposed mechanism of the Fe(II)-promoted rearrangement of 557a–c.
Scheme 163: The reaction of dioxolane 563 with Fe(II) sulfate.
Scheme 164: Fe(II)-promoted rearrangement of 1,2-dioxane 565.
Scheme 165: Fe(II) cysteinate-promoted rearrangement of 1,2-dioxolane 568.
Scheme 166: The transformation of 1,2-dioxanes 572a–c under the action of FeCl2.
Scheme 167: Fe(II) cysteinate-promoted transformation of tetraoxane 574.
Scheme 168: The CoTPP-catalyzed transformation of bicyclic endoperoxides 600a–d.
Scheme 169: The CoTPP-catalyzed transformation of epoxy-1,2-dioxanes.
Scheme 170: The Ru(II)-catalyzed reactions of 1,4-endoperoxide 261g.
Scheme 171: The Ru(II)-catalyzed transformation as a key step in the synthesis of elyiapyrone A (610) from 1,4-...
Scheme 172: Peroxides with antimalarial activity.
Scheme 173: The interaction of iron ions with artemisinin (616).
Scheme 174: The interaction of FeCl2 with 1,2-dioxanes 623, 624.
Scheme 175: The mechanism of reaction 623 and 624 with Fe(II)Cl2.
Scheme 176: The reaction of bicyclic natural endoperoxides G3-factors 631–633 with FeSO4.
Scheme 177: The transformation of terpene cardamom peroxide 639.
Scheme 178: The different ways of the cleavage of tetraoxane 643.
Scheme 179: The LC–MS analysis of interaction of tetraoxane 646 with iron(II)heme 647.
Scheme 180: The rearrangement of 3,6-epidioxy-1,10-bisaboladiene (EDBD, 649).
Scheme 181: Easily oxidized substrates.
Scheme 182: Biopathway of synthesis of prostaglandins.
Scheme 183: The reduction and rearrangements of isoprostanes.
Scheme 184: The partial mechanism for linoleate 658 oxidation.
Scheme 185: The transformation of lipid hydroperoxide.
Scheme 186: The acid-catalyzed cleavage of the product from free-radical oxidation of cholesterol (667).
Scheme 187: Two pathways of catechols oxidation.
Scheme 188: Criegee-like or Hock-like rearrangement of the intermediate hydroperoxide 675 in dioxygenase enzyme...
Scheme 189: Carotinoides 679 cleavage by carotenoid cleavage dioxygenases.
Synthesis and in vitro cytotoxicity of acetylated 3-fluoro, 4-fluoro and 3,4-difluoro analogs of D-glucosamine and D-galactosamine
- Štěpán Horník,
- Lucie Červenková Šťastná,
- Petra Cuřínová,
- Jan Sýkora,
- Kateřina Káňová,
- Roman Hrstka,
- Ivana Císařová,
- Martin Dračínský and
- Jindřich Karban
Beilstein J. Org. Chem. 2016, 12, 750–759, doi:10.3762/bjoc.12.75
- cell growth creates an avenue for their use in the development of anticancer drugs, it also limits their utility as agents to modify the cellular glycome [62]. The cytotoxic activity of peracetylated monofluoro analogs 1, and 4–6, their 1-O-deacetylated derivatives 2, and 49–51, difluoro analogs 7 and
Graphical Abstract
Figure 1: Examples of deoxofluorinated hexosamines.
Scheme 1: Retrosynthetic plan.
Scheme 2: Preparation of starting 2-azido compounds. Reagents and conditions: (a) NaN3, NH4Cl, MeOC2H4OH, 79%...
Scheme 3: Preparation of mono and difluoro analogs of 2-azido-2-deoxy-1,6-anhydro-β-D-gluco- and galactopyran...
Scheme 4: Suggested mechanisms for deoxofluorination at C-3 of 1,6-anhydro-β-D-glucohexopyranose derivatives....
Scheme 5: Formation of oxazoline 41 from 19.
Scheme 6: 1-O-Deacetylation of monofluorinated hexosamines. Reagents and conditions: (a) BnNH2, THF, 62%; (b)...
Three new trixane glycosides obtained from the leaves of Jungia sellowii Less. using centrifugal partition chromatography
- Luíse Azevedo,
- Larissa Faqueti,
- Marina Kritsanida,
- Antonia Efstathiou,
- Despina Smirlis,
- Gilberto C. Franchi Jr,
- Grégory Genta-Jouve,
- Sylvie Michel,
- Louis P. Sandjo,
- Raphaël Grougnet and
- Maique W. Biavatti
Beilstein J. Org. Chem. 2016, 12, 674–683, doi:10.3762/bjoc.12.68
- treatment. Plants also have an important role as a source of antitumoral agents, and several anticancer drugs currently in use are derived from natural sources. Natural products often have selective biological actions due to binding affinities for specific proteins, and have superior chemical diversity and
Graphical Abstract
Figure 1: UPLC profile of the butanol fraction of the leaves of Jungia sellowii after shaking the flask with ...
Figure 2: Structures of compounds 1–3.
Figure 3: COSY and HMBC correlations of compounds 1–3.
Figure 4: NOESY correlations of compounds 1–3.
Figure 5: ECD spectra of compounds 1–3.
Versatile synthesis and biological evaluation of novel 3’-fluorinated purine nucleosides
- Hang Ren,
- Haoyun An,
- Paul J. Hatala,
- William C. Stevens Jr,
- Jingchao Tao and
- Baicheng He
Beilstein J. Org. Chem. 2015, 11, 2509–2520, doi:10.3762/bjoc.11.272
- reactions on the 6-chloropurine nucleosides. Intermediate compounds 31–40 were deprotected with a saturated solution of ammonia in methanol to furnish the desired products 6–15 in 70–92% yields (Table 1). 3’-Fluoro-2-chloropurine nucleosides – cladribine and clofarabine mimics Anticancer drugs cladribine
Graphical Abstract
Figure 1: 6-Subsituted purine 3’-deoxy-3’-fluororibosides 1–15.
Figure 2: 2-Chloro- and 2-aminopurine 3’-deoxy-3’-fluororibosides 16–23.
Figure 3: 3’-Deoxy-3’-fluororibosides constructed from universal intermediate 25.
Scheme 1: Synthesis of 3’-deoxy-3’-fluoropurine ribosides 1–3.
Scheme 2: Synthesis of 6-methylpurine 3’-deoxy-3’-fluororiboside 4.
Scheme 3: Synthesis of 6-substituted purine 3’-deoxy-3’-fluororibosides 5–15.
Scheme 4: Synthesis of 6-substituted 2-chloropurine 3’-deoxy-3’-fluororibosides 16–20.
Scheme 5: Synthesis of 2-aminopurine 3’-deoxy-3’-fluororibosides 21–23.
Synthesis, antimicrobial and cytotoxicity evaluation of new cholesterol congeners
- Mohamed Ramadan El Sayed Aly,
- Hosam Ali Saad and
- Shams Hashim Abdel-Hafez
Beilstein J. Org. Chem. 2015, 11, 1922–1932, doi:10.3762/bjoc.11.208
- bioavailability of anticancer drugs. Thus, SuberAniloHydroxamic acid–cholesterol conjugates (SAHA–cholesterol) [11], cholesterol-based charged liposomes encaging doxorubicin [12] or curcumin [13] showed higher activity compared with the native drugs. Synthetic coumarin-caged cholesterol derivatives, for instance
- and death. This explains why it is down-regulated during carcinogenesis and opens the door for nucleophilic addition of amines to 5,6α-EC as a new lead for developing potential anticancer drugs [15]. Apart from antimicrobial and antiproliferative activities of cholesterol derivatives, other
Graphical Abstract
Figure 1: Structure of ceragenin (CSA-8) and selected cholesterol conjugates.
Scheme 1: Reagents and conditions: (a) CBr4, PPh3, DCM (74%); (b) NaN3, DMF, 100 °C (63%); (c) CuSO4·5H2O, L-...
Scheme 2: Reagents and conditions: (a) NaN3, DMF, 100 °C (9b, 47%); (b) CuSO4·5H2O, L-AsAc, THF/H2O [11a, n =...
Scheme 3: Reagents and conditions: CuSO4·5H2O, L-AsAc, THF/H2O (96%).
Scheme 4: Reagents and conditions: (a) 1, TMSOTF, CH3CN, rt (74%); (b) NaOMe, MeOH (84%); (c) NaOH; HCl (pH 5...
Scheme 5: Reagents and conditions: (a) 9a, TMSOTF, DCM, rt (19%); (b) 10, CuSO4·5H2O, L-AsAc, THF/H2O (62%); ...
Scheme 6: Reagents & conditions: (a) Propargyl bromide, NaH, Et2O/DMF (quant. for both 26 and 30); (b) 3, CuSO...
Scheme 7: Reagents and conditions: (a) Bu2SnO, MeOH; propargyl bromide, TBAI, Tol (92%); (b) CuSO4·5H2O, L-As...
Figure 2: In vitro antimicrobial activity of some new cholesterol derivatives against E.coli, S. aureus. A. f...
Figure 3: Cytotoxicity effect of some new cholesterol derivatives on the PC3 cell line. Doxorubicin (Dox) was...
Pyridinoacridine alkaloids of marine origin: NMR and MS spectral data, synthesis, biosynthesis and biological activity
- Louis P. Sandjo,
- Victor Kuete and
- Maique W. Biavatti
Beilstein J. Org. Chem. 2015, 11, 1667–1699, doi:10.3762/bjoc.11.183
- selectivity according to the reported IC50 data. A linear or angular arrangement, as found in ascididemin and neoamphimedine structures, respectively, are two interesting backbones that could be used as starting points in the search for new anticancer drugs. Pyridoacridones containing fused rings with 1,4
Graphical Abstract
Figure 1: Fragments produced by the FAB–MS of dehydrokuanoniamine B (20) [42].
Figure 2: Fragments produced by the EIMS of sagitol (26) [55].
Figure 3: Fragments produced by the EIMS of styelsamine B (4) [45].
Figure 4: Fragments produced by the EIMS of styelsamine D (6) [45].
Figure 5: Fragments produced by the EIMS of subarine (37) [40].
Scheme 1: Synthesis of styelsamine B (4) and cystodytin J (1) [58].
Scheme 2: Synthesis of sebastianine A (38) and its regioisomer 39 [59].
Scheme 3: Synthesis route A of neoamphimedine (12) [61].
Scheme 4: Synthesis route B of neoamphimedine (12) [62].
Scheme 5: Synthesis of arnoamines A (40) and B (41) [63].
Scheme 6: Synthesis of ascididemin (42) [65].
Scheme 7: Synthesis of subarine (37) [66,67].
Scheme 8: Synthesis of demethyldeoxyamphimedine (9) [68].
Scheme 9: Synthesis of pyridoacridine analogues related to ascididemin (42) [70].
Scheme 10: Synthesis of analogues of meridine (56) [71].
Scheme 11: Synthesis of bulky pyridoacridine as eilatin (58) [72].
Scheme 12: Synthesis of AK37 (59), analogue of kuanoniamine A (60) [73].
Figure 6: Biosynthesis pathway I [74].
Figure 7: Reaction illustrating catechol and kynuramine as possible biosynthetic precursors [75].
Figure 8: Biosynthesis pathway B deduced from the feeding experiment A using labelled precursors [76].
Figure 9: Proposed biosynthesis pathway [47].
Figure 10: 4H-Pyrido[2,3,4-kl]acridin-4-one as a cytotoxic pharmacophore.
Figure 11: 7H-Pyrido[2,3,4-kl]acridine as a cytotoxic pharmacophore.
Figure 12: 9H-Quinolino[4,3,2-de][1,10]phenanthrolin-9-one as a cytotoxic pharmacophore.
Figure 13: 8H-Benzo[b]pyrido[4,3,2-de][1,7]phenanthrolin-8-one as a cytotoxic pharmacophore.
Figure 14: Pyrido[4,3,2-mn]pyrrolo[3,2,1-de]acridine as a cytotoxic pharmacophore.
Figure 15: 9H-Pyrido[4,3,2-mn]thiazolo[4,5-b]acridin-9-one and 8H-pyrido[4,3,2-mn]thiazolo[4,5-b]acridine: cyt...
Figure 16: 9H-quinolino[4,3,2-de][1,10]phenanthrolin-9-one as an anti-mycobacterial pharmacophore.
Figure 17: 9H-Quinolino[4,3,2-de][1,10]phenanthrolin-9-one as an antibacterial pharmacophore.
Figure 18: Saturated and less saturated pyridine moieties as aspartyl inhibitor cores.
Figure 19: Iminobenzoquinone and acridone cores as intercalating and TOPO inhibitor motifs found in pyridoacri...
Deproto-metallation of N-arylated pyrroles and indoles using a mixed lithium–zinc base and regioselectivity-computed CH acidity relationship
- Mohamed Yacine Ameur Messaoud,
- Ghenia Bentabed-Ababsa,
- Madani Hedidi,
- Aïcha Derdour,
- Floris Chevallier,
- Yury S. Halauko,
- Oleg A. Ivashkevich,
- Vadim E. Matulis,
- Laurent Picot,
- Valérie Thiéry,
- Thierry Roisnel,
- Vincent Dorcet and
- Florence Mongin
Beilstein J. Org. Chem. 2015, 11, 1475–1485, doi:10.3762/bjoc.11.160
- previously [60]. A2058 cells are highly invasive human epithelial adherent melanoma cells, derived from lymph nodes metastatic cells obtained from a 43 year old male patient. They are tumorigenic at 100% frequency in nude mice, and considered as very resistant to anticancer drugs. All cell culture
Graphical Abstract
Figure 1: Substrates involved in deproto-metallation reaction.
Figure 2: ORTEP diagram (30% probability) of 2e.
Scheme 1: Synthesis of the azole substrates 1f and 2f.
Scheme 2: Deproto-metallation of 1c followed by iodolysis [33].
Scheme 3: Deproto-metallation of 1a and 2a followed by iodolysis.
Scheme 4: Deproto-metallation of 1b and 2b followed by iodolysis.
Scheme 5: Deproto-metallation of 1c and 2c followed by iodolysis.
Figure 3: ORTEP diagrams (30% probability) of 4c, 3d and 3e.
Scheme 6: Deproto-metallation of 1d and 2d followed by iodolysis.
Scheme 7: Deproto-metallation of 1e and 2e followed by iodolysis.
Scheme 8: N-arylation of the iodides 3b, 3d and 4d.
Figure 4: ORTEP diagram (30% probability) of 5d.
Figure 5: Calculated values of pKa(THF) of the compounds 1 and 2, and bromobenzene.
Figure 6: Antiproliferative activity (growth inhibition) of the tested compounds 1a,b,e,f, 2a,b and 5d at con...
Figure 7: Iodides previously formed as major products from the corresponding N-(4-methoxyphenyl)azoles using ...
Gold-catalyzed formation of pyrrolo- and indolo-oxazin-1-one derivatives: The key structure of some marine natural products
- Sultan Taskaya,
- Nurettin Menges and
- Metin Balci
Beilstein J. Org. Chem. 2015, 11, 897–905, doi:10.3762/bjoc.11.101
- and multidrug resistance reversal activity [12][13][14]. Lamellarins 4 with a pyrrolo-oxazinone substructure are also marine natural products and they inhibit the proliferation of cancer cells and therefore are promising candidates for anticancer drugs [15][16][17][18][19][20]. The design and
Graphical Abstract
Figure 1: Structures of some marine natural products 1–4.
Figure 2: Structures 5–7.
Scheme 1: Intramolecular gold(I)-catalyzed cyclization reaction of 8 to give 9 and 10.
Scheme 2: Synthesis of 13 and its reaction with AuCl3.
Scheme 3: Synthesis of 6.
Figure 3: Geometry optimized structures of 6, 7, 30 and 31.
Scheme 4: Reaction of 15 with Au(I)/AgOTf in the presence of EtOH and CD3OD.
Scheme 5: Reaction of 7 with Au(I)/AgOTf in the presence of EtOH.
Scheme 6: Proposed reaction mechanism for the intramolecular gold-catalyzed cyclization followed by EtOH addi...
Formulation development, stability and anticancer efficacy of core-shell cyclodextrin nanocapsules for oral chemotherapy with camptothecin
- Hale Ünal,
- Naile Öztürk and
- Erem Bilensoy
Beilstein J. Org. Chem. 2015, 11, 204–212, doi:10.3762/bjoc.11.22
- higher when incorporated in hybrid CD nanocapsules compared with a DMSO solution. Conclusion: Oral CD nanocapsules indicating increased oral bioavailability might be a promising strategy to maintain the physiological stability and to improve the oral bioavailability of problematic anticancer drugs such
- is the poor aqueous solubility due to the hydrophobicity of most anticancer drugs [3]. Most of the anticancer drugs are formulated with co-solubilizers via intravenous administration; however these co-solubilizers lead to severe side effects restricting both the patient’s quality of life and efficacy
- of the therapy. Another major factor is that anticancer drugs have a wide distribution capacity in the body and owing to non-selective cytotoxicity of these drugs not only the cancer cells but also healthy cells are killed. Due to low therapeutic indices of anticancer drugs, a rapid increase and
Graphical Abstract
Figure 1: Scanning electron microphotographs of A) 6OCAPRO nanocapsules and B) CS-6OCAPRO nanocapsules.
Figure 2: In vitro release profiles of CPT from anionic and cationic CD nanocapsules in pH 1.2 PBS A) in 2 ho...
Figure 3: Cell viability of blank 6OCAPRO and CS-6OCAPRO nanocapsules against L929 cells after 48 h incubatio...
Figure 4: Viability of MCF-7 cells cultured with CPT loaded 6OCAPRO and CS-6OCAPRO nanocapsules in comparison...
Figure 5: Apparent permeability coefficient (Paap) of different CPT formulations: CPT in DMSO solution, CPT l...
Preparation and evaluation of cyclodextrin polypseudorotaxane with PEGylated liposome as a sustained release drug carrier
- Kayoko Hayashida,
- Taishi Higashi,
- Daichi Kono,
- Keiichi Motoyama,
- Koki Wada and
- Hidetoshi Arima
Beilstein J. Org. Chem. 2014, 10, 2756–2764, doi:10.3762/bjoc.10.292
- delivery of anticancer drugs [28]. PEG-LP encapsulating DOX is commercially available as DOXIL/CAELYX® [28]. In addition, PEG-LPs are also utilized as long-circulating drug carriers for protein drugs and nucleic acids [37][38]. Thus, PEG-LPs are representative drug carriers and CD PPRXs of PEG-LPs could be
Graphical Abstract
Figure 1: (A) Photographs and (B) powder X-ray diffraction patterns of precipitates formed by mixing the CD s...
Figure 2: (A) Chemical structures of DSPE and PEG-DSPE, (B) photographs of the γ-CD solutions after adding DO...
Figure 3: (A) FTIR spectra, (B) powder X-ray diffraction patterns, (C) 1H NMR spectrum and (D) proposed parti...
Figure 4: (A) In vitro release profiles of the total DOX from γ-CD PPRX in various volumes of PBS, (B) releas...
The regulation and biosynthesis of antimycins
- Ryan F. Seipke and
- Matthew I. Hutchings
Beilstein J. Org. Chem. 2013, 9, 2556–2563, doi:10.3762/bjoc.9.290
- over-produced in cancer cells that are resistant to apoptosis-inducing chemotherapy agents, so antimycins have great potential as anticancer drugs used in combination with existing chemotherapeutics. Here we review what is known about antimycins, the regulation of the ant gene cluster and the unusual
Graphical Abstract
Figure 1: Antimycins: Antimycins A1, A2, A3, and A4 and non-natural antimycins referenced in the text. Antimy...
Figure 2: Schematic representation of ant biosynthetic gene clusters. L-form ant gene clusters are encoded by...
Figure 3: Proposed biosynthetic pathway for antimycins. The antimycin biosynthetic pathway is described in de...
Figure 4: σAntA comprises a new subfamily of ECF RNA polymerase σ factors. σAntA amino acid sequences were al...
Synthesis and characterization of novel bioactive 1,2,4-oxadiazole natural product analogs bearing the N-phenylmaleimide and N-phenylsuccinimide moieties
- Catalin V. Maftei,
- Elena Fodor,
- Peter G. Jones,
- M. Heiko Franz,
- Gerhard Kelter,
- Heiner Fiebig and
- Ion Neda
Beilstein J. Org. Chem. 2013, 9, 2202–2215, doi:10.3762/bjoc.9.259
- . synthesized maleimide derivatives of doxorubicin and camptothecin. After intravenous administration these designed anticancer drugs bind rapidly to circulating albumin [17][18][19]. Endogenous albumin could be seen as a drug carrier, as it accumulates in solid tumors according to the pathophysiology of tumor
Graphical Abstract
Figure 1: Natural products having a 1,2,4-oxadiazole core.
Figure 2: Examples of 1,2,4-oxadiazole antitumorals.
Scheme 1: Common synthetic strategies toward 1,2,4-oxadiazoles; (a) amidoxime route; (b) 1,3 dipolar cycloadd...
Scheme 2: One-pot synthesis of 4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)aniline (1) by using the amidoxime route....
Figure 3: Molecular structure of 4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)aniline (1). Atoms are drawn as 50% the...
Figure 4: Packing diagram of compound 1. Hydrogen bonds are indicated as dashed lines.
Scheme 3: One-pot synthesis of 4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)aniline (1) by using the 1,3-dipolar cycl...
Figure 5: Molecular structure of 3-tert-butyl-5-(4-nitrophenyl)-1,2,4-oxadiazole (2). Atoms are drawn as 50% ...
Figure 6: Packing diagram of compound (2) showing C–H···O interactions.
Scheme 4: Synthesis of 1-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenyl)pyrrolidine-2,5-dione (4).
Figure 7: Molecular structure of 1-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenyl)pyrrolidine-2,5-dione (4). At...
Figure 8: Molecular structure of 4-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenylamino)-4 oxobutanoate (5). Ato...
Figure 9: Packing diagram of compound (5). Dashed lines indicate hydrogen bonds.
Scheme 5: Synthesis of 1-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenyl)-1H-pyrrole-2,5-dione (7).
Figure 10: Molecular structure of (Z)-4-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenylamino)-4-oxobut-2-enoic ac...
Figure 11: Packing diagram of compound 6. Dashed lines indicate hydrogen bonds.
Figure 12: In vitro antitumor activity of compounds 1, 3–7 toward 11 human tumor cell lines.
Figure 13: Individual IC50 values [µM] of compounds 1, 3–7 in a panel of 11 human tumor cell lines.
Synthesis of meso-substituted dihydro-1,3-oxazinoporphyrins
- Satyasheel Sharma and
- Mahendra Nath
Beilstein J. Org. Chem. 2013, 9, 496–502, doi:10.3762/bjoc.9.53
- tissue, and efficiency in generating reactive oxygen species by the absorption of photons in the visible or near IR region make them ideal candidates for developing effective photodynamic agents. These findings have encouraged researchers to design and synthesize potential targeting anticancer drugs
Graphical Abstract
Scheme 1: Synthesis of dihydro-1,3-benzoxazinoporphyrins.
Scheme 2: Synthesis of dihydro-1,3-naphthoxazinoporphyrins.
Scheme 3: Synthesis of naphtho[e]bis(dihydro-1,3-oxazinoporphyrin) derivatives.
Figure 1: (a) Electronic absorption spectra of free-base porphyrins 6, 8, 14, 16 and 18 in CHCl3 at 298 K. (b...
Thioester derivatives of the natural product psammaplin A as potent histone deacetylase inhibitors
- Matthias G. J. Baud,
- Thomas Leiser,
- Vanessa Petrucci,
- Mekala Gunaratnam,
- Stephen Neidle,
- Franz-Josef Meyer-Almes and
- Matthew J. Fuchter
Beilstein J. Org. Chem. 2013, 9, 81–88, doi:10.3762/bjoc.9.11
- oncogenesis [3][4] and small molecule inhibitors of these pathways have emerged as highly attractive targets for anticancer therapies [5][6]. Inhibitors of epigenetic pathways should not only be useful as anticancer drugs, but also as molecular probes to study the causative relationships between specific
Graphical Abstract
Figure 1: FDA approved HDAC inhibitors for the treatment of CTCL.
Scheme 1: SAR of psammaplin A against zinc-dependant HDACs. Adapted from Baud et al. [20].
Scheme 2: Synthesis of 7–9. Conditions: (i) HCl·H2NOMe, pyridine, rt, 12 h; (ii) EDC, NHS, dioxane, rt, 3 h; ...
Scheme 3: Top: Generation of the fluorescent adduct 11 after reaction of probe 10 with thiols. Bottom left: F...
Figure 2: rHDAC1 was incubated with a predetermined IC50 concentration of 7 (left) and 9 (right) for 1–60 min...
An easily accessible sulfated saccharide mimetic inhibits in vitro human tumor cell adhesion and angiogenesis of vascular endothelial cells
- Grazia Marano,
- Claas Gronewold,
- Martin Frank,
- Anette Merling,
- Christian Kliem,
- Sandra Sauer,
- Manfred Wiessler,
- Eva Frei and
- Reinhard Schwartz-Albiez
Beilstein J. Org. Chem. 2012, 8, 787–803, doi:10.3762/bjoc.8.89
- development not only of new tools for tumor diagnosis and monitoring but also in the design of new anticancer drugs [8]. Attempts have been made to mount an immune response against tumor oligosaccharides by carbohydrate vaccines [9] and also to inhibit adhesive processes, such as the interaction between
- angiogenesis and is currently under investigation in several clinical trials for the treatment of recurrent malignant glioblastoma [48]. GSF, due to its direct anti-tumor and anti-angiogenic effect, may represent a new class of small-molecule anticancer drugs. Although anti-angiogenic drugs such as the
Graphical Abstract
Scheme 1: Synthesis of (4-{[(β-D-galactopyranosyl)oxy]methyl}furan-3-yl)methyl hydrogen sulfate (GSF, 5) and ...
Figure 1: Effects of increasing concentrations of (4-{[(β-D-galactopyranosyl)oxy]methyl}furan-3-yl)methyl hyd...
Figure 2: Inhibition of adhesion of WM-115 cells to fibrinogen (A), or to fibronectin (B) with increasing con...
Figure 3: Inhibition of adhesion of melanoma cells WM-115 to fibronectin-coated plastic by 5 mM (4-{[(β-D-gal...
Figure 4: In silico blind-docking (A, B) and molecular dynamic simulations (C) of (4-{[(β-D-galactopyranosyl)...
Figure 5: Intact cell monolayers of WM-115 cells in 12-well plates were wounded with a 100 µL pipette tip and...
Figure 6: A: Zymograms (color inverted) of serum-free conditioned medium of melanoma cells treated with (4-{[...
Figure 7: Adhesion of HBMEC-60 to extracellular matrix proteins. Prior to the adhesion experiments, HBMEC-60 ...
Figure 8: Effect of (4-{[(β-D-galactopyranosyl)oxy]methyl}furan-3-yl)methyl hydrogen sulfate (GSF) on transmi...
Figure 9: Influence of saccharide mimetics on endothelial networking (matrigel-assay) (A) and tube formation ...
Enantioselective supramolecular devices in the gas phase. Resorcin[4]arene as a model system
- Caterina Fraschetti,
- Matthias C. Letzel,
- Antonello Filippi,
- Maurizio Speranza and
- Jochen Mattay
Beilstein J. Org. Chem. 2012, 8, 539–550, doi:10.3762/bjoc.8.62
- are the elementary units of the RNA and DNA biomacromolecules, and their physiological importance at many different levels [52][53][54] makes them potential candidates as anticancer drugs. The gas-phase study of the intimate interactions between the resorcin[4]arene V and several pyrimidine
Graphical Abstract
Figure 1: Examples of monoexponential decay: The slope of the line directly provides the reaction pseudo-firs...
Figure 2: Example of biexponential decay.
Figure 3: Amidoresorcin[4]arene YS.
Scheme 1: Studied (a) peptidoresorcin[4]arenes and (b) dipeptidic guests.
Figure 4: Catharanthine and vindoline, monomers constituting the anticancer vinblastine and the analogous vin...
Figure 5: Stable conformers of catharanthine.
Figure 6: Global minima of (a) [VS∙H∙T]+ and (b) [VR∙H∙T]+ complexes.
Figure 7: Guests studied in [47].
Figure 8: Selected nucleosides.
Figure 9: Example of molecular logic gate.
Figure 10: Cyclochiral resorcin[4]arenes.
