Org. and Biomol. Chem.

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Synthesis and Tautomerization of Hydroxylated Isoflavones Bearing Heterocyclic Hemi-Aminals

19 November, 2014 - 15:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02137A, PaperMykhailo M Frasinyuk, Svitlana P Bondarenko, Volodymyr P Khilya, Chunming Liu, David Watt, Vitaliy M Sviripa
The aminomethylation of hydroxylated isoflavones with 2-aminoethanol, 3-amino-1-propanol, 4-amino-1-butanol, and 5-amino-1-pentanol in the presence of excess formaldehyde led principally to 9-(2-hydroalkyl)-9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]-oxazin-4-ones 4 and/or the tautomeric 7-hydroxy-8-(1,3-oxazepan-3-ylmethyl)-4H-chromen-4-ones 5. The ratio of...
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Modulation of the charge transfer and photophysical properties in non-fused tetrathiafulvalene-benzothiadiazole derivatives

19 November, 2014 - 15:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02100B, PaperFlavia Pop, Sabine Seifert, Jihane Hankache, Jie Ding, Andreas Hauser, Narcis Avarvari
Bis(thiomethyl)- and bis(thiohexyl)-tetrathiafulvalene-bromo-benzothiadiazoles, containing electron donor tetrathiafulvalene (TTF) and electron acceptor benzothiadiazole (BTD) units, have been prepared by Stille coupling reactions between the TTF-SnMe3 precursors and BTD-Br2. In another series...
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Tuning the pH-triggered self-assembly of dendritic peptide amphiphiles using fluorinated side chains

19 November, 2014 - 15:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02185A, PaperRalph Appel, Sebastian Tacke, Jurgen Klingauf, Pol Besenius
We report the synthesis of a series of anionic dendritic peptide amphiphiles of increasing hydrophobic character. By establishing state diagrams we describe their pH and ionic strength triggered self-assembly into...
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Interactions of Arene Ruthenium Metallaprisms with Human Proteins

19 November, 2014 - 15:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02194K, PaperLydia E. H. Paul, Bruno Therrien, Julien Furrer
Interactions between three hexacationic arene ruthenium metallaprisms, ([(p-cymene)6Ru6(tpt)2(dhnq)3]6+, [(p-cymene)6Ru6(tpt)2(dhbq)3]6+ and [(p-cymene)6Ru6(tpt)2(oxa)3]6+, and a series of human proteins including human serum albumin, transferrin, cytochrome c, myoglobin and ubiquitin have been studied...
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Hydroformylation of olefins and reductive carbonylation of aryl halides with syngas formed ex situ from dehydrogenative decarbonylation of hexane-1,6-diol

19 November, 2014 - 15:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01958J, PaperRobert Madsen, Stig Holden Christensen, Esben Paul Krogh Olsen, Jascha Rosenbaum
A variety of primary alcohols have been investigated as convenient substrates for the ex situ delivery of carbon monoxide and molecular hydrogen in a two-chamber reactor. The gaseous mixture is...
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Indole-Based Novel Small Molecules for the Modulation of Bacterial Signalling Pathways

19 November, 2014 - 15:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02096K, PaperNripendra Nath Biswas, Samuel Kutty, Nicolas Barraud, George M Iskander, A/Prof Renate Griffith, Scott Rice, Mark DP Willcox, David StClair Black, Naresh Kumar
Gram-negative bacteria such as Pseudomonas aeruginosa use N-acylated L-homoserine lactones (AHLs) as autoinducers (AIs) for quorum sensing (QS), a major regulatory and cell-to-cell communication system for social adaptation, virulence factor...
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Selective detection of Al3+ and citric acid with a fluorescent amphiphile

19 November, 2014 - 15:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB02095B, PaperZiya Kostereli, Kay Severin
The assembly and disassembly of a fluorescent amphiphile by Al3+ and citrate, respectively, can be used to sense these analytes by fluorescence spectroscopy.
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A Mild Copper-catalyzed Aerobic Oxidative Thiocyanation of Arylboronic Acids with TMSNCS

19 November, 2014 - 15:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02208D, CommunicationNan Sun, Liusheng Che, Weimin Mo, Baoxiang Hu, Zhenlu Shen, Xinquan Hu
A facile and efficient transformation of arylboronic acids to their corresponding arylthiocyanates has been successfully developed. Based on the CuCl-catalyzed oxidative cross-coupling reaction between arylboronic acids and trimethylsilylisothiocyanate (TMSNCS) under...
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Bioorthogonal labelling of 3-nitrotyrosine in peptides and proteins through diazotisation mediated azidation

19 November, 2014 - 15:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02133A, CommunicationJohn Yee Ng, Jason Wing Hon Wong
A new chemical derivatisation method to functionalise peptide and protein bound 3-nitrotyrosine residues is described. By transforming 3-nitrotyrosine to 3-azidotyrosine, the method enables 'click chemistry'-based labelling of the 3-nitrotyrosine residues...
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Cationic dialkylarylphosphates: new family of bio-inspired cationic lipids for gene delivery.

19 November, 2014 - 15:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01770F, PaperPaul-Alain Jaffres, Stephanie Sandra Le Corre, Nawal Belmadi, Mathieu Berchel, Tony Le GAll, Jean-Pierre Haelters, Pierre Lehn, Tristan Montier
In this work, that aims to synthesize and evaluate new cationic lipids as vectors for gene delivery, we report the synthesis of a series of cationic lipids in which a...
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Bleomycin-induced trans lipid formation in cell membranes and in liposome models

19 November, 2014 - 15:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01924E, PaperAysegul Cort, Tomris Ozben, Anna Sansone, Sebastian Barata-Vallejo, Chryssostomos Chatgilialoglu, C Ferreri
Cell cultures of NTera-2 cells incubated with bleomycin and liposomes as biomimetic models of cell membranes were used for examining novel aspects of drug-metal induced reactivity with unsaturated lipids under...
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Interfacial catalysis of aldol reactions by prolinamide surfactants in reverse micelles

19 November, 2014 - 15:54

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02074J, PaperPremkumar Rathinam Arivalagan, Yan Zhao
Aggregation of prolinamide surfactants in nonpolar solvents enhanced their catalytic activity and gave unusual substrate selectivity in aldol condensations.
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Determination of the Absolute Configuration of Phosphinic Analogues of Glutamate

19 November, 2014 - 15:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01960A, PaperBruno Commare, Delphine Rigault, Isabelle Lemasson, Patrick Deschamps, Alain Tomas, Pascal ROUSSEL, Isabelle Brabet, Cyril Goudet, Jean Phillippe Pin, Frederic R. Leroux, Francoise COLOBERT, Francine Acher
A series of phosphinic glutamate derivatives (e.g. LSP1-2111) have proved to be potent agonists of metabotropic glutamate (mGlu) receptors and shown promising in vivo activity. However, so far all were...
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Allylic and Benzylic sp3 C-H Oxidation in Water

19 November, 2014 - 15:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02017K, PaperWei-Jie Ang, Yulin Lam
A copper-catalyzed method for the oxidation of allylic and benzylic sp3 C-H by aqueous tert-butyl hydroperoxide (TBHP) in water using a recyclable fluorous ligand has been developed. The reaction procedure...
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Self-organizing behaviour of glycosteroidal bolaphiles: insights into lipidic microsegregation

19 November, 2014 - 15:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB02191F, PaperR. Xu, F. Ali-Rachedi, N. M. Xavier, S. Chambert, F. Ferkous, Y. Queneau, S. J. Cowling, E. J. Davis, J. W. Goodby
The synthesis of glycosteroidal bolaphile biomimics are described along with the liquid-crystalline behaviours as a function of increasing aliphatic composition.
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Palladium(0)-catalyzed synthesis of cyclic glucosides

19 November, 2014 - 15:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01975J, PaperXin Huang, Chunling Fu, Shengming Ma
A highly regio- and stereo-selective synthesis of cyclic [small beta]-D-glucosides 3 via Pd(0)-catalyzed coupling cyclization of allenyl [small beta]-D-glucoside 1 and organic iodides in 20-38% yields is reported.
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Post-synthesis DNA Modifications Using a trans-Cyclooctene Click Handle

17 November, 2014 - 15:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02031F, PaperKe Wang, Danzhu Wang, Kaili Ji, Weixuan Chen, Yueqin Zheng, Chaofeng Dai, Binghe Wang
Post-synthesis DNA modification is a very useful method for DNA functionalization. This is achieved by using a modified NTP, which has a handle for further modifications, replacing the corresponding natural...
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1,1-Alkenylboration of diarylphosphino-enynes: convenient synthetic entry to vicinal P/B Lewis pairs at extended conjugated [small pi]-frameworks

17 November, 2014 - 15:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02134G, PaperGuo-Qiang Chen, Gerald Kehr, Constantin G. Daniliuc, Gerhard Erker
Alkenylboranes R-CH[double bond, length as m-dash]CH-B(C6F5)2 undergo carbon-carbon coupling by means of 1,1-alkenylboration with diarylphosphino-enynes to give conjugated hexatriene derivatives that bear a vicinal pair of B(C6F5)2 and PAr2 functionalities at the framework.
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Virtual screening and biological evaluation of novel small molecular inhibitors against protein arginine methyltransferase 1 (PRMT1)

17 November, 2014 - 15:17

Org. Biomol. Chem., 2014, 12,9665-9673
DOI: 10.1039/C4OB01591F, PaperYiqian Xie, Ran Zhou, Fulin Lian, Yan Liu, Limin Chen, Zhe Shi, Naixia Zhang, Mingyue Zheng, Bairong Shen, Hualiang Jiang, Zhongjie Liang, Cheng Luo
Two novel inhibitors against PRMT1 were identified through virtual screening and biochemical assays. Their binding with PRMT1 was validated and they also displayed an anti-proliferation effect in three cancer cell lines.
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Copper-catalysed intramolecular O-arylation: a simple and efficient method for benzoxazole synthesis

17 November, 2014 - 15:17

Org. Biomol. Chem., 2014, 12,9696-9701
DOI: 10.1039/C4OB02068E, PaperFengtian Wu, Jie Zhang, Qianbing Wei, Ping Liu, Jianwei Xie, Haojie Jiang, Bin Dai
An efficient protocol has been developed for the copper-catalysed intramolecular cyclization of N-(2-iodo-/bromo-/chloro-phenyl)benzamides for the synthesis of 2-substituted benzoxazoles.
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