Org. and Biomol. Chem.

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Aliphatic acid-conjugated antimicrobial peptides - potential agents with anti-tumor, multidrug resistance-reversing activity and enhanced stability

29 June, 2015 - 23:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB00752F, PaperXin Deng, Qianqian Qiu, Ke Ma, Xuekun Wang, Wenlong Huang, Hai Qian
We have designed and synthesized a series of aliphatic acid-conjugated peptides. Biological evaluation revealed that these peptides showed improved anti-tumor activity, plasma stability over the lead compound, and also multidrug resistance-reversing effects on multidrug-resistant cells.
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Design, synthesis and biological evaluation of novel FGFR inhibitors bearing an indazole scaffold

29 June, 2015 - 23:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB00778J, PaperJian Liu, Xia Peng, Yang Dai, Wei Zhang, Sumei Ren, Jing Ai, Meiyu Geng, Yingxia Li
Fibroblast growth factor receptor (FGFR) is a potential target for cancer therapy.
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Two-step one-pot synthesis of dihydropyrazinones as Xaa-Ser dipeptide isosteres through morpholine acetal rearrangement

29 June, 2015 - 23:17

Org. Biomol. Chem., 2015, 13,7013-7019
DOI: 10.1039/C5OB00783F, PaperElena Lenci, Riccardo Innocenti, Gloria Menchi, Cristina Faggi, Andrea Trabocchi
The synthesis of the uncommon dihydropyrazinone ring was accomplished by taking advantage of the ring rearrangement of N-acylated morpholine acetal derived from serine under acidic treatment and in the presence of 2,6-lutidine, resulting in a constrained Xaa-Ser dipeptide isostere.
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Reductive alkylation of active methylene compounds with carbonyl derivatives, calcium hydride and a heterogeneous catalyst

29 June, 2015 - 23:17

Org. Biomol. Chem., 2015, 13,7067-7075
DOI: 10.1039/C5OB00849B, PaperCarole Guyon, Marie-Christine Duclos, Marc Sutter, Estelle Metay, Marc Lemaire
A one-pot two-step reaction (Knoevenagel condensation - reduction of the double bond) has been developed using calcium hydride as a reductant in the presence of a supported noble metal catalyst.
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Double-headed nucleotides introducing thymine nucleobases in the major groove of nucleic acid duplexes

29 June, 2015 - 23:17

Org. Biomol. Chem., 2015, 13,7040-7049
DOI: 10.1039/C5OB00872G, PaperMichael Dalager, Nicolai K. Andersen, Pawan Kumar, Poul Nielsen, Pawan K. Sharma
Four double-headed nucleotides are synthesized via Sonogashira and Suzuki couplings and introduced into nucleic acid duplexes.
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Base catalyzed synthesis of bicyclo[3.2.1]octane scaffolds

29 June, 2015 - 23:17

Org. Biomol. Chem., 2015, 13,6940-6943
DOI: 10.1039/C5OB00933B, CommunicationRegis Boehringer, Philippe Geoffroy, Michel Miesch
A base-catalyzed and time controlled reaction of 1,3-cyclopentanediones tethered to activated olefins afforded in high yields either bicyclo[3.2.1]octane-6,8-dione or bicyclo[3.2.1]octane-6-carboxylate derivatives.
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An update on new methods to synthesize cyclotetrapeptides

29 June, 2015 - 23:17

Org. Biomol. Chem., 2015, 13,6906-6921
DOI: 10.1039/C5OB00880H, Review ArticleLuis M. De Leon Rodriguez, Andreas J. Weidkamp, Margaret A. Brimble
This review provides an account of the reported methods used for the synthesis of cyclotetrapeptides.
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Copper-catalyzed efficient direct amidation of 2-methylquinolines with amines

29 June, 2015 - 23:17

Org. Biomol. Chem., 2015, 13,6944-6948
DOI: 10.1039/C5OB00915D, CommunicationHao Xie, Yunfeng Liao, Shuqing Chen, Ya Chen, Guo-Jun Deng
A copper catalyzed efficient procedure for quinoline-2-carboxamides formation via direct amidation of 2-methylquinolines under oxygen is described.
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Discovery of novel Bcr-Abl inhibitors with diacylated piperazine as the flexible linker

27 June, 2015 - 22:54

Org. Biomol. Chem., 2015, 13,7050-7066
DOI: 10.1039/C5OB00430F, PaperXiaoyan Pan, Jinyun Dong, Yaling Shi, Ruili Shao, Fen Wei, Jinfeng Wang, Jie Zhang
Forty-two compounds with flexible diacylated piperazine linkers were designed, synthesized and evaluated as novel Bcr-Abl inhibitors.
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Synthesis of DNA fragments containing 2[prime or minute]-deoxy-4[prime or minute]-selenonucleoside units using DNA polymerases: comparison of dNTPs with O, S and Se at the 4[prime or minute]-position in replication

27 June, 2015 - 22:54

Org. Biomol. Chem., 2015, 13,6949-6952
DOI: 10.1039/C5OB00941C, CommunicationN. Tarashima, T. Sumitomo, H. Ando, K. Furukawa, T. Ishida, N. Minakawa
The first synthesis of 4[prime or minute]-selenoDNA was achieved using 4[prime or minute]-selenothymidine triphosphate by taking advantage of its bioequivalence against DNA polymerases.
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Tetrabutylammonium iodide-catalyzed oxidative coupling of enamides with sulfonylhydrazides: synthesis of [small beta]-keto-sulfones

27 June, 2015 - 22:54

Org. Biomol. Chem., 2015, 13,7084-7090
DOI: 10.1039/C5OB00742A, PaperYucai Tang, Ye Zhang, Kaifeng Wang, Xiaoqing Li, Xiangsheng Xu, Xiaohua Du
A novel synthetic route toward pharmaceutically interesting [small beta]-keto-sulfone derivatives via TBAI/TBHP-mediated oxidative coupling of readily prepared enamides with sulfonylhydrazides is described.
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Synthesis of N-vinylindoles through copper catalyzed cyclization reaction of N-(2-alkynylphenyl)imine

27 June, 2015 - 22:54

Org. Biomol. Chem., 2015, 13,6931-6934
DOI: 10.1039/C5OB00746A, CommunicationZhi-Qiang Wang, Xu Zhang, Lin-Tao Yu, Wu-Tao Mao, Chang-Zhong Chen, Kun Xu
A Cu(II)-catalyzed cyclization reaction of N-(2-alkynylphenyl)imine to synthesize substituted N-vinylindoles is developed.
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An efficient and practical approach to trifluoromethylthiolation of [small alpha]-haloketones/[small alpha]-haloarylmethanes

25 June, 2015 - 22:17

Org. Biomol. Chem., 2015, 13,6935-6939
DOI: 10.1039/C5OB00858A, CommunicationMin Jiang, Fangxia Zhu, Haoyue Xiang, Xing Xu, Lianfu Deng, Chunhao Yang
An efficient and practical approach to the trifluoromethylthiolation of [small alpha]-haloketones/[small alpha]-haloarylmethanes was developed, providing an unprecedentedly easy entry to various [small alpha]-SCF3-substituted ketones/arylmethanes.
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Aggregation of asphaltene model compounds using a porphyrin tethered to a carboxylic acid

23 June, 2015 - 21:54

Org. Biomol. Chem., 2015, 13,6984-6991
DOI: 10.1039/C5OB00836K, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Matthias Schulze, Marc P. Lechner, Jeffrey M. Stryker, Rik R. Tykwinski
Two model compounds are used in NMR spectroscopic studies to probe aggregation toward unraveling the mysteries of intermolecular interactions in asphaltenes, which are the heaviest portions of petroleum.
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Rapid and scalable synthesis of innovative unnatural [small alpha],[small beta] or [gamma]-amino acids functionalized with tertiary amines on their side-chains

23 June, 2015 - 21:54

Org. Biomol. Chem., 2015, 13,7020-7026
DOI: 10.1039/C5OB00828J, PaperSeverine Schneider, Hussein Ftouni, Songlin Niu, Martine Schmitt, Frederic Simonin, Frederic Bihel
We report a selective ruthenium catalyzed reduction of tertiary amides on the side chain of Fmoc-Gln-OtBu derivatives, leading to innovative unnatural [small alpha],[small beta] or [gamma]-amino acids functionalized with tertiary amines.
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Organocatalytic asymmetric Michael addition of 1-acetylcyclohexene and 1-acetylcyclopentene to nitroolefins

23 June, 2015 - 21:54

Org. Biomol. Chem., 2015, 13,7076-7083
DOI: 10.1039/C5OB00878F, PaperUtpal Nath, Ankush Banerjee, Bidhan Ghosh, Subhas Chandra Pan
The first organocatalytic asymmetric Michael reaction between [small alpha]-branched enones namely 1-acetylcyclohexene, 1-acetylcyclopentene and 1-acetylcyclobutene with nitroolefins has been developed using primary amines as catalysts.
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Synthesis and in vitro cytotoxicity of cross-conjugated prostaglandin A and J series and their hydroxy derivatives

23 June, 2015 - 21:54

Org. Biomol. Chem., 2015, 13,7000-7012
DOI: 10.1039/C5OB00550G, PaperRemigiusz Zurawinski, Marian Mikolajczyk, Marcin Cieslak, Karolina Krolewska, Julia Kazmierczak-Baranska
An efficient synthetic protocol for the synthesis of enantiomerically pure cyclopentenone prostaglandin derivatives is described and the anticancer activity of these derivatives was determined.
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Surface-promoted aggregation of amphiphilic quadruplex ligands drives their selectivity for alternative DNA structures

23 June, 2015 - 21:54

Org. Biomol. Chem., 2015, 13,7034-7039
DOI: 10.1039/C5OB00692A, PaperAurelien Laguerre, Yi Chang, Marc Pirrotta, Nicolas Desbois, Claude P. Gros, Eric Lesniewska, David Monchaud
The surface-promoted aggregation of a structurally fine-tuned TMPyP4 derivative allows for the straightforward visualization of the quadruplex/ligand interactions via high-speed AFM.
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Palladium-catalyzed ortho-acyloxylation of N-nitrosoanilines via direct sp2 C-H bond activation

23 June, 2015 - 21:54

Org. Biomol. Chem., 2015, 13,6958-6964
DOI: 10.1039/C5OB00691K, PaperDan-Dan Li, Yi-Xuan Cao, Guan-Wu Wang
The palladium-catalyzed N-nitroso-directed ortho-acyloxylation of N-nitrosoanilines has been demonstrated via sp2 C-H activation with PhI(OAc)2 as the oxidant and Ac2O/AcOH (1 : 1) or C2H5CO2H as the reaction medium.
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Detection of boronic acid derivatives in cells using a fluorescent sensor

23 June, 2015 - 21:54

Org. Biomol. Chem., 2015, 13,6927-6930
DOI: 10.1039/C5OB00753D, CommunicationYoshihide Hattori, Miki Ishimura, Youichirou Ohta, Hiroshi Takenaka, Tsubasa Watanabe, Hiroki Tanaka, Koji Ono, Mitsunori Kirihata
To develop a detection method for boronic acid derivatives, boron-chelating ligands were synthesized as fluorescent sensors for boronic acid derivatives.
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