Org. and Biomol. Chem.

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Synthesis of new generation triazolyl- and isoxazolyl-containing 6-nitro-2,3-dihydroimidazooxazoles as anti-TB agents: in vitro, structure-activity relationship, pharmacokinetics and in vivo evaluation

16 March, 2015 - 21:17

Org. Biomol. Chem., 2015, 13,3610-3624
DOI: 10.1039/C5OB00054H, PaperGurunadham Munagala, Kushalava Reddy Yempalla, Samsher Singh, Sumit Sharma, Nitin Pal Kalia, Vikrant Singh Rajput, Sunil Kumar, Sanghapal D. Sawant, Inshad Ali Khan, Ram A. Vishwakarma, Parvinder Pal Singh
Promising nitroimidazoloxazole scaffold gives another novel triazolyl-containing 6-nitro-2,3-dihydroimidazooxazole as anti-TB lead.
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Copper(II) bromide-catalyzed intramolecular decarboxylative functionalization to form a C(sp3)-O bond for the synthesis of furo[3,2-c]coumarins

16 March, 2015 - 21:17

Org. Biomol. Chem., 2015, 13,3602-3609
DOI: 10.1039/C4OB02490G, PaperW. L. Zhang, S. N. Yue, Y. M. Shen, H. Y. Hu, Q.-H. Meng, H. Wu, Y. Liu
Copper(II) bromide-catalyzed intramolecular decarboxylative functionalization to form a C(sp3)-O bond has been developed.
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Chiral nanostructuring of multivalent macrocycles in solution and on surfaces

16 March, 2015 - 21:17

Org. Biomol. Chem., 2015, 13,3593-3601
DOI: 10.1039/C4OB02643H, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Marco Caricato, Arnaud Delforge, Davide Bonifazi, Daniele Dondi, Andrea Mazzanti, Dario Pasini
A chiral, multivalent macrocycle assembles upon metal-pyridine coordination into ordered nanostructures in solution and on surfaces.
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Recent advances in development of imidazo[1,2-a]pyrazines: synthesis, reactivity and their biological applications

16 March, 2015 - 21:17

Org. Biomol. Chem., 2015, 13,3525-3555
DOI: 10.1039/C4OB01380H, Review ArticleRicha Goel, Vijay Luxami, Kamaldeep Paul
The synthesis, reactivity and multifarious biological activities at the different positions of imidazo[1,2-a]pyrazines are concisely discussed in this review.
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[gamma]-(S)-Trifluoromethyl proline: evaluation as a structural substitute of proline for solid state 19F-NMR peptide studies

12 March, 2015 - 20:17

Org. Biomol. Chem., 2015, 13,3171-3181
DOI: 10.1039/C5OB00034C, Review ArticleVladimir Kubyshkin, Sergii Afonin, Sezgin Kara, Nediljko Budisa, Pavel K. Mykhailiuk, Anne S. Ulrich
[gamma]-(S)-Trifluoromethyl proline has been evaluated as a structural label for solid state 19F-NMR studies of polypeptides.
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Hemisynthesis of deuteriated adenosylhopane and conversion into bacteriohopanetetrol by a cell-free system from Methylobacterium organophilum

12 March, 2015 - 20:17

Org. Biomol. Chem., 2015, 13,3393-3405
DOI: 10.1039/C4OB02560A, PaperWenjun Liu, Anne Bodlenner, Michel Rohmer
(2H2)Adenosylhopane was synthesised via a reaction sequence including a cross metathesis followed by N22H2 reduction of the resulting olefin.
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Buffer catalyzed cleavage of uridylyl-3[prime or minute],5[prime or minute]-uridine in aqueous DMSO: comparison to its activated analog, 2-hydroxypropyl 4-nitrophenyl phosphate

12 March, 2015 - 20:17

Org. Biomol. Chem., 2015, 13,3484-3492
DOI: 10.1039/C4OB02682A, PaperL. Lain, H. Lonnberg, T. A. Lonnberg
In 80% aq. DMSO, buffer catalysis of the cleavage of UpU is significant but weaker than with HPNP.
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One-step protecting-group-free synthesis of azepinomycin in water

12 March, 2015 - 20:17

Org. Biomol. Chem., 2015, 13,3378-3381
DOI: 10.1039/C5OB00210A, PaperAdam J. Coggins, Derek A. Tocher, Matthew W. Powner
pH-dependent one-step multi-gram synthesis of azepinomycin in water.
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Copper(II)-catalyzed electrophilic amination of quinoline N-oxides with O-benzoyl hydroxylamines

10 March, 2015 - 19:54

Org. Biomol. Chem., 2015, 13,3207-3210
DOI: 10.1039/C5OB00135H, CommunicationGang Li, Chunqi Jia, Kai Sun, Yunhe Lv, Feng Zhao, Kexiao Zhou, Hankui Wu
Copper acetate-catalyzed C-H bond functionalization amination of quinoline N-oxides was achieved using O-benzoyl hydroxylamine as an electrophilic amination reagent, thereby affording the desired products in moderate to excellent yields.
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Photo-induced conjugation of tetrazoles to modified and native proteins

10 March, 2015 - 19:54

Org. Biomol. Chem., 2015, 13,3202-3206
DOI: 10.1039/C4OB02025A, CommunicationWinna Siti, Amit Kumar Khan, Hans-Peter M. de Hoog, Bo Liedberg, Madhavan Nallani
The direct addition of a water-soluble PEG-tetrazole to tryptophan residues in native proteins is demonstrated.
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Homocoupling versus reduction of radicals: an experimental and theoretical study of Ti(III)-mediated deoxygenation of activated alcohols

10 March, 2015 - 19:54

Org. Biomol. Chem., 2015, 13,3462-3469
DOI: 10.1039/C4OB02290D, PaperConsuelo Prieto, Jose A. Gonzalez Delgado, Jesus F. Arteaga, Martin Jaraiz, Jose L. Lopez-Perez, Alejandro F. Barrero
A detailed study corroborates that the Ti(III)-mediated reductive deoxygenation of activated -OH proceeds via an allyl(benzyl)-radical and allyl(benzyl)-Ti, which is protonated, regioselectively in the case of allylic derivatives.
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PhI(OAc)2-mediated functionalisation of unactivated alkenes for the synthesis of pyrazoline and isoxazoline derivatives

10 March, 2015 - 19:54

Org. Biomol. Chem., 2015, 13,3457-3461
DOI: 10.1039/C5OB00029G, PaperXiao-Qiang Hu, Guoqiang Feng, Jia-Rong Chen, Dong-Mei Yan, Quan-Qing Zhao, Qiang Wei, Wen-Jing Xiao
A PhI(OAc)2-promoted radical cyclization of [small beta],[gamma]-unsaturated hydrazones and oximes has been developed for an efficient synthesis of pyrazolines and isoxazolines.
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Exploring a cascade Heck-Suzuki reaction based route to kinase inhibitors using design of experiments

10 March, 2015 - 19:54

Org. Biomol. Chem., 2015, 13,3382-3392
DOI: 10.1039/C4OB02694B, PaperAndreas Ekebergh, Christine Lingblom, Peter Sandin, Christine Wenneras, Jerker Martensson
A fused tricyclic system with kinase inhibiting properties was assembled via a palladium catalyzed tandem reaction. The reaction was optimized using statistical experimental design.
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A highly diastereoselective Friedel-Crafts reaction of indoles with isatin-derived N-sulfinyl ketimines towards the efficient synthesis of chiral tetrasubstituted 3-indolyl-3-aminooxindoles

10 March, 2015 - 19:54

Org. Biomol. Chem., 2015, 13,3363-3370
DOI: 10.1039/C5OB00063G, PaperJian-Ping Chen, Wen-Wen Chen, Yi Li, Ming-Hua Xu
A Lewis acid promoted highly diastereoselective asymmetric Friedel-Crafts alkylation of indoles with isatin-derived N-tert-butanesulfinyl ketimines is described.
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A prominent bathochromic shift effect of indole-containing diarylethene derivatives

10 March, 2015 - 19:54

Org. Biomol. Chem., 2015, 13,3470-3475
DOI: 10.1039/C4OB02619E, PaperHong-Bo Cheng, Yao-Dong Huang, Lina Zhao, Xu Li, Hai-Chen Wu
Bisindole diarylethene derivatives exhibit a strong bathochromic shift effect in photochromism compared with bisbenzothiophene diarylethene.
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[gamma]-Aminoalcohol rearrangement applied to pentahydroxylated azepanes provides pyrrolidines epimeric to homoDMDP

10 March, 2015 - 19:54

Org. Biomol. Chem., 2015, 13,3446-3456
DOI: 10.1039/C5OB00050E, PaperY. Jagadeesh, A. T. Tran, B. Luo, N. Auberger, J. Desire, S. Nakagawa, A. Kato, Y. Zhang, M. Sollogoub, Y. Bleriot
Exploiting a [gamma]-aminoalcohol rearrangement, pentahydroxylated azepanes are converted to pyrrolidines that are epimeric to homoDMDP, a potent glycosidase inhibitor.
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The first water-soluble bowl complex: molecular recognition of acetate by the biomimetic tris(imidazole) Zn(II) system at pH 7.4

10 March, 2015 - 19:54

Org. Biomol. Chem., 2015, 13,3194-3197
DOI: 10.1039/C4OB02514H, CommunicationStephanie Rat, Jerome Gout, Olivia Bistri, Olivia Reinaud
The bowl-shaped cavity-ligand based on resorcinarene has been successfully transposed into a water-soluble version that readily binds Zn(II) and acetate at physiological pH.
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Exploration of the active site of [small beta]4GalT7: modifications of the aglycon of aromatic xylosides

10 March, 2015 - 19:54

Org. Biomol. Chem., 2015, 13,3351-3362
DOI: 10.1039/C4OB02632B, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence.Anna Siegbahn, Karin Thorsheim, Jonas Stahle, Sophie Manner, Christoffer Hamark, Andrea Persson, Emil Tykesson, Katrin Mani, Gunilla Westergren-Thorsson, Goran Widmalm, Ulf Ellervik
[small beta]4GalT7 is an essential enzyme in the biosynthesis of glycosaminoglycans. Modifications at the anomeric center of aromatic xylosides change the galactosylation efficiency significantly.
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Synthesis of (Z)-(arylamino)-pyrazolyl/isoxazolyl-2-propenones as tubulin targeting anticancer agents and apoptotic inducers

10 March, 2015 - 19:54

Org. Biomol. Chem., 2015, 13,3416-3431
DOI: 10.1039/C4OB02449D, PaperAhmed Kamal, Vangala Santhosh Reddy, Anver Basha Shaik, G. Bharath Kumar, M. V. P. S. Vishnuvardhan, Sowjanya Polepalli, Nishant Jain
A new class of pyrazole conjugates were synthesized and evaluated for their antiproliferative activity in human cancer cell lines: 9a, 9b and 9f significantly inhibited cell growth as well as tubulin polymerization.
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Fluorination of 2-substituted benzo[b]furans with Selectfluor[trade mark sign]

10 March, 2015 - 19:54

Org. Biomol. Chem., 2015, 13,3190-3193
DOI: 10.1039/C4OB02691H, CommunicationMingliang Wang, Xixi Liu, Lu Zhou, Jidong Zhu, Xun Sun
An efficient protocol was developed to access 3-fluoro-2-hydroxy-2-substituted benzo[b]furans with Selectfluor[trade mark sign] as the fluorinating reagent in MeCN and water. By utilizing SOCl2/Py as the dehydrating agent, the compounds above were readily converted to 3-fluorinated, 2-substituted benzo[b]furans in high yields.
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