Investigations of thiol-modified phenol derivatives for the use in thiol–ene photopolymerizations

• Sebastian Reinelt,
• Monir Tabatabai,
• Urs Karl Fischer,
• Norbert Moszner,
• Andreas Utterodt and
• Helmut Ritter

Beilstein J. Org. Chem. 2014, 10, 1733–1740, doi:10.3762/bjoc.10.180

• initiated after 120 s. Synthetic route for the preparation of the thiol-functionalized bisphenols 10a and 10b. Synthetic route for the preparation of thiol-functionalized phenol derivatives 14a–c and 17 using the Claisen rearrangement and the radical addition of thioacetic acid as key steps. Chemical

• structures of components utilized in the present study. Flexural strength and flexural modulus of elasticity before and after storage in H2O as well as the conversion. All samples contained a stoichiometric amount of TATATO and the below-mentioned thiol, 0.5 wt % initiator (K69) and 0.04 wt % Q1301. Flexural

Synthesis of zearalenone-16-β,D-glucoside and zearalenone-16-sulfate: A tale of protecting resorcylic acid lactones for regiocontrolled conjugation

• Hannes Mikula,
• Julia Weber,
• Dennis Svatunek,
• Philipp Skrinjar,
• Gerhard Adam,
• Rudolf Krska,
• Christian Hametner and
• Johannes Fröhlich

Beilstein J. Org. Chem. 2014, 10, 1129–1134, doi:10.3762/bjoc.10.112

• mycotoxins, especially altered derivatives formed through conjugation to sugar moieties or sulfate, emerge after metabolization by living plants. Due to changed chemical structures and properties compared to the parent mycotoxins, these conjugates can usually not be detected applying standard analytical

Tailoring of organic dyes with oxidoreductive compounds to obtain photocyclic radical generator systems exhibiting photocatalytic behavior

• Christian Ley,
• Julien Christmann,
• Ahmad Ibrahim,
• Luciano H. Di Stefano and
• Xavier Allonas

Beilstein J. Org. Chem. 2014, 10, 936–947, doi:10.3762/bjoc.10.92

• )benzoate (EDB) were obtained from Aldrich, 2-(4-methoxyphenyl)-4,6-bis(trichloromethyl)-1,3,5-triazine (TA) was gifts from PCAS (France). Their chemical structures are given in Scheme 1. Evolution of RB concentration as a function of irradiation time (λ = 532 nm, 9 mW·cm−3); insert: absorption spectra

• , respectively. Evolution of radical concentrations TA•− and EDB•+ together with [RB] in photocatalytic system. Chemical structures of RB, EDB and TA. Type II PIS mechanisms. PS: photosensitizer; 1,3PS*: singlet and triplet PS excited states; PS•+: oxidized PS; A: electron acceptor coinitiator; A•−: reduced

An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles

• Marcus Baumann and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2013, 9, 2265–2319, doi:10.3762/bjoc.9.265

Topochemical control of the photodimerization of aromatic compounds by γ-cyclodextrin thioethers in aqueous solution

• Hai Ming Wang and
• Gerhard Wenz

Beilstein J. Org. Chem. 2013, 9, 1858–1866, doi:10.3762/bjoc.9.217

• , respectively [50]. Chemical structures of selected aromatic guests: anthracene, ANT; acenaphthylene, ACE; and coumarin, COU. Structures of γ-CD and γ-CD thioethers 1–7. 1H NMR spectrum of the photo product of ACE in the presence of γ-CD thioether 3 in CDCl3. Schematic drawing of the ACE photodimers in γ-CD: a

The rapid generation of isothiocyanates in flow

• Marcus Baumann and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2013, 9, 1613–1619, doi:10.3762/bjoc.9.184

• advanced chemical structures and more direct scaling of bulk producing reactions [1][2][3][4][5][6][7][8][9][10]. Consequently, the chemical literature is growing at a precipitous rate with numerous examples of key chemical transformations having been further optimised or improved upon when conducted

Space filling of β-cyclodextrin and β-cyclodextrin derivatives by volatile hydrophobic guests

• Sophie Fourmentin,
• Anca Ciobanu,
• David Landy and
• Gerhard Wenz

Beilstein J. Org. Chem. 2013, 9, 1185–1191, doi:10.3762/bjoc.9.133

• . The most stable conformation for each inclusion compound was then completely relaxed (convergence fixed to 0.05 kJ Å−1 mol−1). Inclusion enthalpy was evaluated by the difference between the most stable inclusion-compound conformation and the free species. Chemical structures of β-CD 1, hydroxypropyl-β

• -CD 2, and β-CD-thioethers 3 and 4. Chemical structures of the benzene and cyclohexane derivatives, with their calculated molecular volumes, VG = M/dNA in Å3, with M molecular weight, d density, NA Avogadro’s number. Chromatogram obtained by HS-GC for a mixture of aromatic guests (1 ppm) in water

Study on the total synthesis of velbanamine: Chemoselective dioxygenation of alkenes with PIFA via a stop-and-flow strategy

• Huili Liu,
• Kuan Zheng,
• Xiang Lu,
• Xiaoxia Wang and
• Ran Hong

Beilstein J. Org. Chem. 2013, 9, 983–990, doi:10.3762/bjoc.9.113

• indole alkaloids comprise a large category of alkaloids with diverse biological activities [1]. Their complex chemical structures and applications in pharmaceuticals have sparked numerous synthetic efforts in the past few decades. Dimeric indole alkaloids such as vinblastine (3) (Scheme 1) still inspire

Zanthoxoaporphines A–C: Three new larvicidal dibenzo[de,g]quinolin-7-one alkaloids from Zanthoxylum paracanthum (Rutaceae)

• Fidelis N. Samita,
• Louis P. Sandjo,
• Isaiah O. Ndiege,
• Ahmed Hassanali and
• Wilber Lwande

Beilstein J. Org. Chem. 2013, 9, 447–452, doi:10.3762/bjoc.9.47

• ). Isolation and purification of the constituent compounds was achieved through conventional chromatographic methods. The chemical structures of the isolated compounds were determined on the basis of UV, IR, NMR and MS data, and confirmed by comparison with those reported in the literature. The larvicidal

Thermotropic and lyotropic behaviour of new liquid-crystalline materials with different hydrophilic groups: synthesis and mesomorphic properties

• Alexej Bubnov,
• Miroslav Kašpar,
• Věra Hamplová,
• Ute Dawin and
• Frank Giesselmann

Beilstein J. Org. Chem. 2013, 9, 425–436, doi:10.3762/bjoc.9.45

• as TL3 and TL4 [26][27][28]) or both types of these hydrophilic groups together and an additional photosensitive azo group in the molecular core (denoted as TL5) have been designed, synthesized and studied (see Table 1 for the chemical structures). Compound TL4 with a decyloxy end group and a hexyl

A new family of four-ring bent-core nematic liquid crystals with highly polar transverse and end groups

• Kalpana Upadhyaya,
• Venkatesh Gude,
• Golam Mohiuddin and
• Rao V. S. Nandiraju

Beilstein J. Org. Chem. 2013, 9, 26–35, doi:10.3762/bjoc.9.4

• -alkoxybenzylidene)amino)benzoates 1a–1c. To make a comparison with the mesomorphic 1a–1c, other compounds 1d–1f were prepared following the same procedure adopted for 1a by using the appropriate reagents as outlined in Scheme 2. The chemical structures of the final compounds 1 were confirmed by spectral techniques

• and elemental analysis. The analytical data are in good agreement with their chemical structures. The main observed FTIR peaks confirmed the intramolecular H-bonding of OH…N at 3184~3186 cm−1, CN stretching at 2220 cm−1, C=O stretching of an ester at 1737~1741 cm−1, C=N stretching of an imine at 1602

Chemical–biological characterization of a cruzain inhibitor reveals a second target and a mammalian off-target

• Jonathan W. Choy,
• Clifford Bryant,
• Claudia M. Calvet,
• Patricia S. Doyle,
• Shamila S. Gunatilleke,
• Siegfried S. F. Leung,
• Kenny K. H. Ang,
• Steven Chen,
• Jiri Gut,
• Juan A. Oses-Prieto,
• Jonathan B. Johnston,
• Michelle R. Arkin,
• Alma L. Burlingame,
• Jack Taunton,
• Matthew P. Jacobson,
• James M. McKerrow,
• Larissa M. Podust and
• Adam R. Renslo

Beilstein J. Org. Chem. 2013, 9, 15–25, doi:10.3762/bjoc.9.3

• the use of cell-based counter assays that can detect action at specific targets or signaling pathways of interest. Activity-based probes can serve as useful tools to verify on-target action during the course of chemical optimization campaigns. Chemical structures of vinylsulfone-based cruzain

• - ergosta-7,24-diene-3β-ol (episterol), [M]•+ = m/z 470; e - ergosta-8,24-diene-3β-ol (fecosterol), [M]•+ = m/z 470; f - lanosterol, [M]•+ = m/z 498; g - 4-methylepisterol, [M]•+ = m/z 484; h - eburicol, [M]•+ = m/z 512; i - 24-ethyl-7,24(24’)-encholestadien-3β-ol, [M]•+ = m/z 484. Chemical structures of

Bioactive selaginellins from Selaginella tamariscina (Beauv.) Spring

• Chao Yang,
• Yutian Shao,
• Kang Li and
• Wujiong Xia

Beilstein J. Org. Chem. 2012, 8, 1884–1889, doi:10.3762/bjoc.8.217

• )ethynyl)biphenyl-2-yl)(4-hydroxyphenyl)methylene]cyclohexa-2,5-dien-1-one, named as selaginellin O. The chemical structures of selaginellin M (2), selaginellin (3) and selaginellin A (4) were identified by spectral analysis by 1D and 2D NMR spectroscopy and high-resolution MS. Their 1H and 13C NMR data

A new approach toward the total synthesis of (+)-batzellaside B

• Jolanta Wierzejska,
• Shin-ichi Motogoe,
• Yuto Makino,
• Tetsuya Sengoku,
• Masaki Takahashi and
• Hidemi Yoda

Beilstein J. Org. Chem. 2012, 8, 1831–1838, doi:10.3762/bjoc.8.210

• class of biologically potent piperidine alkaloids and related analogues. Examples of naturally occurring iminosugars. The chemical structures of (+)-batzellasides A–C (1a–c). Our previous approach to (+)-batzellaside B and retrosynthetic analysis for the new synthetic strategy. Reagents and conditions

Dimerization of a cell-penetrating peptide leads to enhanced cellular uptake and drug delivery

• Jan Hoyer,
• Ulrich Schatzschneider,
• Michaela Schulz-Siegmund and
• Ines Neundorf

Beilstein J. Org. Chem. 2012, 8, 1788–1797, doi:10.3762/bjoc.8.204

• at different concentrations after 1 h incubation. Experiments were conducted in triplicate with n = 2. Error bars represent the standard deviation. Synthesis of (sC18)2 bioconjugates (a) and chemical structures of the coupled anti-tumor agents (b). Mtt: 4-methyltrityl chloride; Dde: 1-(4,4-dimethyl

Molecular solubilization of fullerene C₆₀ in water by γ-cyclodextrin thioethers

• Hai Ming Wang and
• Gerhard Wenz

Beilstein J. Org. Chem. 2012, 8, 1644–1651, doi:10.3762/bjoc.8.188

• . Size distributions of the aqueous C60 dispersions after filtration, produced by stirring C60 in 6mM γ-CD solution in DMF/toluene (v/v 1:1) according to procedure c) [42]: (a) by intensity and (b) by volume. Chemical structures of γ-CD and γ-CD thioether 1–7 used to solubilize C60 in water. Mechanistic

Supramolecular hydrogels formed from poly(viologen) cross-linked with cyclodextrin dimers and their physical properties

• Yoshinori Takashima,
• Yang Yuting,
• Miyuki Otsubo,
• Hiroyasu Yamaguchi and
• Akira Harada

Beilstein J. Org. Chem. 2012, 8, 1594–1600, doi:10.3762/bjoc.8.182

• viologen derivatives Figure 1 depicts the chemical structures of the cyclodextrin dimers (α,α-CD dimer, α,β-CD dimer, and β,β-CD dimer) and pyridyl derivatives (PyC10Py and viologen polymer (VP)). The α,α-CD and β,β-CD dimers are prepared by reacting the corresponding 6-amino-CDs and terephthalic acid

• measured at 20 °C. The sample concentration was adjusted to 1.0 wt %. Chemical structures of the CD dimer (α,α-CD dimer, α,β-CD dimer, and β,β-CD dimer) and guest derivatives [PyC10Py and viologen polymer (VP)]. Bromonium anions are omitted in guest derivatives. Photographs of hydrogelation with various

The crystal structure of the Dess–Martin periodinane

• Albert Schröckeneder,
• Desiree Stichnoth,
• Peter Mayer and
• Dirk Trauner

Beilstein J. Org. Chem. 2012, 8, 1523–1527, doi:10.3762/bjoc.8.172

• , 142.32, 135.87, 133.94, 131.87, 126.59, 126.02, 20.54, 20.39; IR (ATR) : 1699.9, 1670.6. The chemical structures of DMP (1), 2-iodobenzoic acid (2), IBX (3) and 4. ORTEP diagram (50% probability level) of 1 with numbering scheme. Supramolecular structure of 1 with halogen bonds and selected hydrogen

Exploring chemical diversity via a modular reaction pairing strategy

• Joanna K. Loh,
• Sun Young Yoon,
• Thiwanka B. Samarakoon,
• Alan Rolfe,
• Patrick Porubsky,
• Benjamin Neuenswander,
• Gerald H. Lushington and
• Paul R. Hanson

Beilstein J. Org. Chem. 2012, 8, 1293–1302, doi:10.3762/bjoc.8.147

• method described previously [40], by using standard H-aware 3D BCUT descriptors comparing against the MLSMR screening set (ca. 7/2010; ~330,000 unique chemical structures). Guided by this library design analysis, benzoxathiazocine 1,1-dioxides scaffolds 1–8 and amines {1–10} were chosen to generate the

Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix, Part II: Iridomyrmecins

• Robert Hilgraf,
• Nicole Zimmermann,
• Lutz Lehmann,
• Armin Tröger and
• Wittko Francke

Beilstein J. Org. Chem. 2012, 8, 1256–1264, doi:10.3762/bjoc.8.141

• cis- and trans-fused iridoid lactones. 70 eV EI-mass spectrum of compounds Y and Z of Alloxysta victrix. Chemical structures of all eight stereoisomers of trans-fused iridomyrmecins and their gas chromatographic retention times (min) on FFAP and on a cyclodextrin column (cyclo). For experimental

Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix, Part I: Dihydronepetalactones

• Nicole Zimmermann,
• Robert Hilgraf,
• Lutz Lehmann,
• Daniel Ibarra and
• Wittko Francke

Beilstein J. Org. Chem. 2012, 8, 1246–1255, doi:10.3762/bjoc.8.140

• signaling pathways between primary parasitoids and hyperparasitoids. In order to gain further information about the chemical structures and the biological significance of corresponding signals, we examined the volatile components of pentane extracts from dissected heads as well as headspace volatiles of

Similarity analysis, synthesis, and bioassay of antibacterial cyclic peptidomimetics

• Workalemahu M. Berhanu,
• Mohamed A. Ibrahim,
• Girinath G. Pillai,
• Alexander A. Oliferenko,
• Levan Khelashvili,
• Farukh Jabeen,
• Bushra Mirza,
• Farzana Latif Ansari,
• Ihsan ul-Haq,
• Said A. El-Feky and
• Alan R. Katritzky

Beilstein J. Org. Chem. 2012, 8, 1146–1160, doi:10.3762/bjoc.8.128

• dissimilarity can be quantified and how synthetic efforts can be focused towards novel active compounds. It would be beneficial to be able to draw practical conclusions (even if approximate) based solely on the chemical structures of existing agents. In the case of cyclic peptides, the complex cyclomatic

Formation of smectic phases in binary liquid crystal mixtures with a huge length ratio

• Nadia Kapernaum,
• Friederike Knecht,
• C. Scott Hartley,
• Jeffrey C. Roberts,
• Robert P. Lemieux and
• Frank Giesselmann

Beilstein J. Org. Chem. 2012, 8, 1118–1125, doi:10.3762/bjoc.8.124

• (adapted from [14]). (a) Layer spacing of the SmF and the SmC phase of the pure compound PhP16 in dependence of the temperature T. (b) Tilt angle θ versus reduced temperature T−Tc for the pure compound PhP16 in the SmF and in the SmC phase. Chemical structures and phase-transition temperatures of the

Synthetic glycopeptides and glycoproteins with applications in biological research

• Ulrika Westerlind

Beilstein J. Org. Chem. 2012, 8, 804–818, doi:10.3762/bjoc.8.90

• for the preparation of complex glycopeptides have been drastically improved. The need for homogenous glycopeptides and glycoproteins with defined chemical structures to study diverse biological phenomena further enhances the development of methodologies. Selected recent advances in synthesis and

An easy α-glycosylation methodology for the synthesis and stereochemistry of mycoplasma α-glycolipid antigens

• Yoshihiro Nishida,
• Yuko Shingu,
• Yuan Mengfei,
• Kazuo Fukuda,
• Hirofumi Dohi,
• Sachie Matsuda and
• Kazuhiro Matsuda

Beilstein J. Org. Chem. 2012, 8, 629–639, doi:10.3762/bjoc.8.70

• and characterized by other groups [11][12][13][14]. Absolute chemical structures of GGPL-I [15] and GGPL–III [16] have already been established by chemical syntheses of stereoisomers; these α-glycolipids have a common chemical backbone of 3-O-(α-D-glucopyranosyl)-sn-glycerol carrying phosphocholine at

• ): [M + Na]+ calcd for C57H108O11Na, 991.7789; found, 991.7832. Absolute chemical structures of M. fermentans α-glycolipid antigens, GGPL-I and GGPl-III (GGPL: Glycosyl-sn-glycerophospholipid). 1H NMR spectra of I-a and I-b (500 MHz, 25 °C, CDCl3/CD3OD 10:1). The assignment of sn-glycerol methylene