Conformational preferences of fluorine-containing agrochemicals and their implications for lipophilicity prediction

• Daniela Rodrigues Silva,
• Joyce K. Daré and
• Matheus P. Freitas

Beilstein J. Org. Chem. 2020, 16, 2469–2476, doi:10.3762/bjoc.16.200

• soil sorption and bioconcentration of organic compounds. Since the C–F bond is the most polar in organic chemistry, the orientation of fluorine substituents originating from the rotation around C–C(F) bonds should affect the polarity and, consequently, the physicochemical and biological properties of

• substituents originated from the rotation of fluorine-containing C–C bonds should affect the polarity and, therefore, the physicochemical and biological properties of organofluorine compounds. However, there is a lack of studies that explain how these well-known conformational effects directly alter

Access to highly substituted oxazoles by the reaction of α-azidochalcone with potassium thiocyanate

• Mysore Bhyrappa Harisha,
• Pandi Dhanalakshmi,
• Rajendran Suresh,
• Raju Ranjith Kumar and
• Shanmugam Muthusubramanian

Beilstein J. Org. Chem. 2020, 16, 2108–2118, doi:10.3762/bjoc.16.178

• ][22][23][24][25][26]. Some oxazoles play a significant role in biological properties such as TRPV1 antagonistical activity, antifungal, analgesic, anti-inflammatory, antiproliferative, antileukemia, anticancer [27][28][29][30][31][32] and enzyme inhibitory activities [33][34][35][36][37][38][39][40

Synthesis of new dihydroberberine and tetrahydroberberine analogues and evaluation of their antiproliferative activity on NCI-H1975 cells

• Giacomo Mari,
• Lucia De Crescentini,
• Serena Benedetti,
• Francesco Palma,
• Stefania Santeusanio and
• Fabio Mantellini

Beilstein J. Org. Chem. 2020, 16, 1606–1616, doi:10.3762/bjoc.16.133

• , there have been only few studies that concern the biological properties of functionalized DHBER. Attracted by the potentiality of this latter compound, we have realized the preparation of new arylhydrazono-functionalized DHBERs, starting from BER and some α-bromohydrazones. On the other hand, also the

• [37][38]. Unlike BER, there have been few studies that concern the biological properties of functionalized DHBER. Attracted by the potentiality of this latter compound, we have realized the preparation of new arylhydrazono-functionalized DHBERs that were tested in vitro for their biological activity

• insertion in the original molecule of different functions with their own peculiar features. Often, the biological properties of the resultant derivatives are not simply attributable to the sum of the characteristics shown by the individual moieties, but synergistic effects can increase their effectiveness

Fluorinated phenylalanines: synthesis and pharmaceutical applications

• Laila F. Awad and
• Mohammed Salah Ayoup

Beilstein J. Org. Chem. 2020, 16, 1022–1050, doi:10.3762/bjoc.16.91

• protein–protein and protein–ligand interactions and consequently metabolic processes [20][21]. Fluorinated phenylalanines (FPhe) have been incorporated into various proteins and enzymes [22][23][24][25] with advantageous biophysical, chemical, and biological properties, and their effect on the stability

• development of efficient synthetic protocols to FAAs. Among them, a range of fluorinated phenylalanines emerged, that have enhanced the biophysical, chemical and biological properties of bioactives. Accordingly, synthetic approaches to five distinct classes of fluorinated analogues were reviewed here

Cation-induced ring-opening and oxidation reaction of photoreluctant spirooxazine–quinolizinium conjugates

• Phil M. Pithan,
• Sören Steup and
• Heiko Ihmels

Beilstein J. Org. Chem. 2020, 16, 904–916, doi:10.3762/bjoc.16.82

• -binding properties to be used as DNA-sensitive fluorescent probes in cell imaging [60][61][62] or as photoswitchable DNA ligands [63]. Therefore, we were interested in a combination of the photochromic properties of the spirooxazine moiety with the advantageous photophysical and biological properties of

Reaction of indoles with aromatic fluoromethyl ketones: an efficient synthesis of trifluoromethyl(indolyl)phenylmethanols using K₂CO₃/n-Bu₄PBr in water

• Thanigaimalai Pillaiyar,
• Masoud Sedaghati and
• Gregor Schnakenburg

Beilstein J. Org. Chem. 2020, 16, 778–790, doi:10.3762/bjoc.16.71

• into organic molecules can dramatically influence their physiochemical and biological properties in comparison with non-fluorinated analogs [18] (see compounds I and II in Figure 1). Many pharmaceuticals and agrochemicals developed in recent decades have either a fluorine atom or a trifluoromethyl

• preparation of 3,3'-, and 3,6'-DIMs, which are known to possess a wide variety of biological activities, including anti-inflammatory, and anticancer effects. Additionally, trifluoromethyl(indolyl)phenylmethanols itselft have various biological properties including anti-HIV activity. The developed new

A systematic review on silica-, carbon-, and magnetic materials-supported copper species as efficient heterogeneous nanocatalysts in “click” reactions

• Pezhman Shiri and
• Jasem Aboonajmi

Beilstein J. Org. Chem. 2020, 16, 551–586, doi:10.3762/bjoc.16.52

• ], antiparkinsonian [6], and anticancer [10] properties. Particularly, triazoles illustrate distinguished moieties well distributed in natural products with biological properties [2][3][4][9][10], including antimicrobial [2], antibacterial [3], antifungal [3], anti-HIV [4], and anticancer [10] activities. One of the

Functionalization of the imidazo[1,2-a]pyridine ring in α-phosphonoacrylates and α-phosphonopropionates via microwave-assisted Mizoroki–Heck reaction

• Damian Kusy,
• Agata Wojciechowska,
• Joanna Małolepsza and
• Katarzyna M. Błażewska

Beilstein J. Org. Chem. 2020, 16, 15–21, doi:10.3762/bjoc.16.3

• of compounds from a common precursor and enables efficient generation of new chemical entities. Imidazo[1,2-a]pyridine constitutes an appealing scaffold in medicinal chemistry. It is present in a number of compounds, which exhibit many interesting biological properties. Its privileged character is

Extension of the 5-alkynyluridine side chain via C–C-bond formation in modified organometallic nucleosides using the Nicholas reaction

• Renata Kaczmarek,
• Dariusz Korczyński,
• James R. Green and
• Roman Dembinski

Beilstein J. Org. Chem. 2020, 16, 1–8, doi:10.3762/bjoc.16.1

• common framework for materials with potent biological properties [6][7][8][9][10]. Modification on this site of the nucleobase usually does not interfere with Watson–Crick base pairing. For example, C-5-modified pyrimidines are well tolerated by commercial polymerases [11][12]. Alkynyl modifications not

Diversity-oriented synthesis of spirothiazolidinediones and their biological evaluation

• Sambasivarao Kotha,
• Gaddamedi Sreevani,
• Lilya U. Dzhemileva,
• Milyausha M. Yunusbaeva,
• Usein M. Dzhemilev and
• Vladimir A. D’yakonov

Beilstein J. Org. Chem. 2019, 15, 2774–2781, doi:10.3762/bjoc.15.269

• represent an important class of nitrogen-containing biologically active compounds which exhibit various biological properties, such as antiviral, antibacterial and anticancer, etc. [55][56][57][58]. Recently, the use of 1,2,3-triazole derivatives as drug candidates has been increased for clinical therapy of

Fluorinated maleimide-substituted porphyrins and chlorins: synthesis and characterization

• Valentina A. Ol’shevskaya,
• Elena G. Kononova and
• Andrei V. Zaitsev

Beilstein J. Org. Chem. 2019, 15, 2704–2709, doi:10.3762/bjoc.15.263

• chlorins for the development of PDT therapeutics and dependence of their biological properties on the structure of peripheral substituents, we developed a simple synthetic approach for new maleimide derivatives of the fluorinated porphyrins and chlorins. We also believe the synthetic potential of maleimide

In water multicomponent synthesis of low-molecular-mass 4,7-dihydrotetrazolo[1,5-a]pyrimidines

• Irina G. Tkachenko,
• Sergey A. Komykhov,
• Vladimir I. Musatov,
• Svitlana V. Shishkina,
• Viktoriya V. Dyakonenko,
• Vladimir N. Shvets,
• Mikhail V. Diachkov,
• Valentyn A. Chebanov and
• Sergey M. Desenko

Beilstein J. Org. Chem. 2019, 15, 2390–2397, doi:10.3762/bjoc.15.231

• biological properties. They have been reported to have anticancer [1], antimicrobial [2][3] and antioxidant [3] activities and to act as inhibitors of hepatitis B virus [4]. The dihydro derivatives of tetrazolo[1,5-a]pyrimidines belong to a bit special kind of dihydropyrimidines due to the strong electron

Fluorescent phosphorus dendrimers excited by two photons: synthesis, two-photon absorption properties and biological uses

• Anne-Marie Caminade,
• Artem Zibarov,
• Eduardo Cueto Diaz,
• Aurélien Hameau,
• Maxime Klausen,
• Kathleen Moineau-Chane Ching,
• Jean-Pierre Majoral,
• Jean-Baptiste Verlhac,
• Olivier Mongin and
• Mireille Blanchard-Desce

Beilstein J. Org. Chem. 2019, 15, 2287–2303, doi:10.3762/bjoc.15.221

• modifications, on the terminal functions [28][29], at the core [30] or linked to the core [31], and in the branches [32] have been achieved. In this review, we will gather the syntheses, fluorescence properties, and some biological properties of phosphorhydrazone dendrimers bearing in some part of their

• two different locations in the structure of the dendrimers, and will report at the end the biological properties. Review The synthesis of phosphorhydrazone dendrimers necessitates two steps to build one generation. Starting from a core having P–Cl functions, such as the hexachlorocyclotriphosphazene

• confinement in the double layer dendrimer has a detrimental influence on the TPA properties [63]. Biological properties of dendrimers having TPA properties Most of the water-soluble fluorescent dendrimers shown in the previous paragraphs have been synthesized for diverse biological purposes. The first type of

Regioselective Pd-catalyzed direct C1- and C2-arylations of lilolidine for the access to 5,6-dihydropyrrolo[3,2,1-ij]quinoline derivatives

• Hai-Yun Huang,
• Haoran Li,
• Thierry Roisnel,
• Jean-François Soulé and
• Henri Doucet

Beilstein J. Org. Chem. 2019, 15, 2069–2075, doi:10.3762/bjoc.15.204

• methodology provides a straightforward access to several lilolidine derivatives from commercially available compounds via one, two or three C–H bond functionalization steps allowing to tune their biological properties. Keywords: catalysis: C–C bond formation; C–H bond activation; lilolidine; palladium

• 10 mol % of CuI as catalyst in DMF at 100 °C. The late stage C–H bond functionalization of molecules represents a powerful method for the easy screening of the biological properties of compounds containing a bioactive unit. Since the seminal work by Ohta et al. on the Pd-catalyzed C–H bond

• nicely. Therefore, this methodology provides a straightforward access to a wide variety of α- and β-(hetero)aryl-substituted lilolidines allowing to tune or modify their biological properties. Structures of lilolidine, tivantinib and tarazepide. Access to α- and β-arylated lilolidine derivatives

N-(1-Phenylethyl)aziridine-2-carboxylate esters in the synthesis of biologically relevant compounds

• Iwona E. Głowacka,
• Aleksandra Trocha,
• Andrzej E. Wróblewski and
• Dorota G. Piotrowska

Beilstein J. Org. Chem. 2019, 15, 1722–1757, doi:10.3762/bjoc.15.168

• , respectively. The latter compound as an unprotected acid was identified as a component of immunosuppressive thalassospiramide A [95] and siderophores called crochelins [96]. On the other hand, the former one was used in the synthesis of edenine A and D analogues [97] to study their biological properties. When

• as components of a variety of plants and exhibit a wide range of biological properties including inhibition of glucosidases [102]. When the aziridine epoxide 162 was treated with acetic acid the aziridine ring cleavage was observed to give the epoxyaldehyde 178 (Scheme 45) [94]. Catalytic

Steroid diversification by multicomponent reactions

• Leslie Reguera,
• Cecilia I. Attorresi,
• Javier A. Ramírez and
• Daniel G. Rivera

Beilstein J. Org. Chem. 2019, 15, 1236–1256, doi:10.3762/bjoc.15.121

• exploitation of the MCR potential in the rapid diversification of steroidal products for screening of their pharmaceutical and biological properties. We expect this review serves as inspiration for the MCR community to further explore the scope of steroids in the development of new reactions and methods

Novel (2-amino-4-arylimidazolyl)propanoic acids and pyrrolo[1,2-c]imidazoles via the domino reactions of 2-amino-4-arylimidazoles with carbonyl and methylene active compounds

• Victoria V. Lipson,
• Tetiana L. Pavlovska,
• Nataliya V. Svetlichnaya,
• Anna A. Poryvai,
• Nikolay Yu. Gorobets,
• Erik V. Van der Eycken,
• Irina S. Konovalova,
• Svetlana V. Shiskina,
• Alexander V. Borisov,
• Vladimir I. Musatov and
• Alexander V. Mazepa

Beilstein J. Org. Chem. 2019, 15, 1032–1045, doi:10.3762/bjoc.15.101

• metabolites of marine sponges with interesting biological properties has received considerable attention from both chemists and pharmacologists. In the middle of 2000s, the authors of the studies [17][18][19] proposed a facile one-pot two-step procedure for the synthesis of diversely substituted 2

Solid-phase synthesis of biaryl bicyclic peptides containing a 3-aryltyrosine or a 4-arylphenylalanine moiety

• Iteng Ng-Choi,
• Àngel Oliveras,
• Lidia Feliu and
• Marta Planas

Beilstein J. Org. Chem. 2019, 15, 761–768, doi:10.3762/bjoc.15.72

• ; cross-coupling; cyclization; macrocycles; solid-phase synthesis; Introduction Monocyclic and bicyclic peptides are acquiring a relevant interest in current drug discovery. They display improved biological properties over their acyclic counterparts and, at the same time, they are suitable to modulate

• amino acids [11]. Cyclic peptides containing biaryl linkages constitute attractive targets. On the one hand, a wide range of biaryl natural products have been reported to display interesting biological properties, such as biphenomycins, arylomycins and glycopeptide antibiotics [4]. On the other hand

Synthesis and biological activity of methylated derivatives of the Pseudomonas metabolites HHQ, HQNO and PQS

• Sven Thierbach,
• Max Wienhold,
• Susanne Fetzner and
• Ulrich Hennecke

Beilstein J. Org. Chem. 2019, 15, 187–193, doi:10.3762/bjoc.15.18

• effect of methylation of AQs on their biological properties more systematically. To this end, we prepared selectively methylated derivatives of the most important heptyl-AQs including HHQ, HQNO and PQS derivatives. These synthetic compounds were tested for their antimicrobial properties against S. aureus

Ring-closing-metathesis-based synthesis of annellated coumarins from 8-allylcoumarins

• Christiane Schultze and
• Bernd Schmidt

Beilstein J. Org. Chem. 2018, 14, 2991–2998, doi:10.3762/bjoc.14.278

• tested for bacteriostatic activity [73] and insect-antifeedant activity [74], respectively. A common denominator of these reports is that a thorough investigation into the spectral and biological properties of these compounds is hampered by unsatisfactory yields and selectivities if classical coumarin

Synthesis of a tyrosinase inhibitor by consecutive ethenolysis and cross-metathesis of crude cashew nutshell liquid

• Jacqueline Pollini,
• Valentina Bragoni and
• Lukas J. Gooßen

Beilstein J. Org. Chem. 2018, 14, 2737–2744, doi:10.3762/bjoc.14.252

• estimated CNSL production of 1.2 million tons per year [5]. CNSL is a mixture of phenolic compounds such as anacardic acid (1), cardol and cardanol, each bearing a C-15 side chain in meta-position to the hydroxy group with a varying degree of unsaturation [6]. CNSL exhibits a broad range of biological

• properties and industrial applications, for instance in surfactants, plasticizers, resins, soft materials and diverse medical applications [7]. Isolated via cold-press or solvent extraction processes, it contains predominantly anacardic acid (1). Upon distillation or any other thermal treatment, anacardic

Stereoselective total synthesis and structural revision of the diacetylenic diol natural products strongylodiols H and I

• Pamarthi Gangadhar,
• Sayini Ramakrishna,
• Ponneri Venkateswarlu and
• Pabbaraja Srihari

Beilstein J. Org. Chem. 2018, 14, 2313–2320, doi:10.3762/bjoc.14.206

• continue to attract significant interest owing to their structural architectures and impressive biological properties that include antibacterial [3], anticancer [4][5][6], antiviral [7] and neuritogenic activities [8]. Watanabe et al. [9][10] have isolated strongylodiols A–J (1–10, Figure 1) [11] from the

Investigation of the electrophilic reactivity of the biologically active marine sesquiterpenoid onchidal and model compounds

• Melissa M. Cadelis and
• Brent R. Copp

Beilstein J. Org. Chem. 2018, 14, 2229–2235, doi:10.3762/bjoc.14.197

• binneyi) also exhibit biological properties including feeding deterrence, antibacterial and anticholinesterase activities. Chemical reactivity studies using polygodial (1), scalaradial (2) and caulerpenyne (3) have demonstrated evidence of pyrrole formation upon reaction with primary amines, with

Synthesis and photophysical studies of a multivalent photoreactive Ru^II-calix[4]arene complex bearing RGD-containing cyclopentapeptides

• Sofia Kajouj,
• Lionel Marcelis,
• Alice Mattiuzzi,
• Adrien Grassin,
• Damien Dufour,
• Pierre Van Antwerpen,
• Didier Boturyn,
• Eric Defrancq,
• Mathieu Surin,
• Julien De Winter,
• Pascal Gerbaux,
• Ivan Jabin and
• Cécile Moucheron

Beilstein J. Org. Chem. 2018, 14, 1758–1768, doi:10.3762/bjoc.14.150

• its receptor [44][45][46], clustered RGD-containing compounds were developed and were shown to exhibit attractive biological properties for the imaging of tumors [47][48][49][50] and for the targeted drug delivery [51][52][53]. In the course of designing phototherapeutic agents that could specifically

Oligonucleotide analogues with cationic backbone linkages

• Melissa Meng and
• Christian Ducho

Beilstein J. Org. Chem. 2018, 14, 1293–1308, doi:10.3762/bjoc.14.111

• anionic nucleic acids is only scarcely understood and will require further research efforts. Studies on the biological properties of (partially) zwitterionic and cationic oligonucleotide analogues in cellular systems, in particular with respect to their cellular uptake, are currently only available for