Org. and Biomol. Chem.

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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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Peptide 2-formylthiophenol esters do not proceed through a Ser/Thr ligation pathway, but participate in a peptide aminolysis to enable peptide condensation and cyclization

23 June, 2015 - 21:54

Org. Biomol. Chem., 2015, 13,6922-6926
DOI: 10.1039/C5OB00825E, CommunicationChun Ling Tung, Clarence T. T. Wong, Xuechen Li
Peptide thiol salicylaldehyde esters unexpectedly do not follow a Ser/Thr ligation pathway, but proceed towards a peptide aminolysis in DMSO.
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meso-Tetraphenylporphyrin with a pi-system extended by fusion with anthraquinone

23 June, 2015 - 21:54

Org. Biomol. Chem., 2015, 13,6977-6983
DOI: 10.1039/C5OB00884K, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Mikhail A. Filatov, Ernesta Heinrich, Katharina Landfester, Stanislav Baluschev
Fusion of a porphyrin with anthraquinone through the synthesis of a suitably substituted pyrrole that can be cyclotetramerized and the optical properties of the resulting molecular system are described.
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Mild electrophilic trifluoromethylthiolation of ketones with trifluoromethanesulfanamide

23 June, 2015 - 21:54

Org. Biomol. Chem., 2015, 13,6992-6999
DOI: 10.1039/C5OB00960J, PaperWei Wu, Xuxue Zhang, Fang Liang, Song Cao
A straightforward and convenient approach for trifluoromethylthiolation of various acyclic and cyclic ketones with PhNHSCF3 is described. The reaction proceeds smoothly in the presence of acetyl chloride at room temperature and affords [small alpha]-trifluoromethylthiolated ketones in fair to good yields.
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Recent developments and applications of the Cadiot-Chodkiewicz reaction

23 June, 2015 - 21:54

Org. Biomol. Chem., 2015, 13,6891-6905
DOI: 10.1039/C5OB00697J, Review ArticleK. S. Sindhu, Amrutha P. Thankachan, P. S. Sajitha, Gopinathan Anilkumar
The classical heterocoupling of a 1-haloalkyne with a terminal alkyne catalyzed by copper salts in the presence of a base for the synthesis of unsymmetrical diynes is termed the Cadiot-Chodkiewicz coupling reaction.
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The origin of the anomeric effect: probing the impacts of stereoelectronic interactions

23 June, 2015 - 21:54

Org. Biomol. Chem., 2015, 13,6965-6976
DOI: 10.1039/C5OB00585J, PaperNeda Hasanzadeh, Davood Nori-Shargh, Mahdieh Farzipour, Bahareh Ahmadi
To gain further insight on the origin of the anomeric effect, the correlations between SE, EM, PETR, bond-orders, donor and acceptor orbital energies and occupancies, structural parameters and configurational behavior of dihalo-1,4-oxathianes were investigated.
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Chelate effects in sulfate binding by amide/urea-based ligands

23 June, 2015 - 21:54

Org. Biomol. Chem., 2015, 13,6953-6957
DOI: 10.1039/C5OB00618J, PaperChuandong Jia, Qi-Qiang Wang, Rowshan Ara Begum, Victor W. Day, Kristin Bowman-James
Chelate and mini-chelate effects on sulfate binding was explored for six amide-, amide/amine-, urea-, and urea/amine-based ligands in water-mixed DMSO-d6. The urea hosts were highly selective for SO42-, and displayed enhanced binding and greater tolerance for increasing water content as the number of chelate groups increased.
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Truce-Smiles rearrangement of substituted phenyl ethers

21 June, 2015 - 21:17

Org. Biomol. Chem., 2015, 13,6754-6765
DOI: 10.1039/C5OB00812C, PaperJoel R. Kosowan, Zemane W'Giorgis, Ravneet Grewal, Tabitha E. Wood
This study of the Truce-Smiles rearrangement has revealed interesting tandem reactions, unprecedented systematic substituent effects, and new mechanistic insight.
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Mitochondrially targeted redox probe reveals the variations in oxidative capacity of the haematopoietic cells

17 June, 2015 - 20:17

Org. Biomol. Chem., 2015, 13,6686-6689
DOI: 10.1039/C5OB00928F, CommunicationAmandeep Kaur, Kurt W. L. Brigden, Timothy F. Cashman, Stuart T. Fraser, Elizabeth J. New
NpFR2 is a fluorescent sensor that can reversibly measure changes in the mitochondrial redox environment.
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Gold and silver catalysis: from organic transformation to bioconjugation

17 June, 2015 - 20:17

Org. Biomol. Chem., 2015, 13,6667-6680
DOI: 10.1039/C5OB00407A, Review ArticleVanessa Kar-Yan Lo, Anna On-Yee Chan, Chi-Ming Che
A summary of gold (including AuNPs, Au(I) and Au(III) complexes) and silver(I) catalysis and their application in bioconjugation reactions.
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Synthesis of tetraarylpyridines by chemo-selective Suzuki-Miyaura reactions of 3,5-dibromo-2,6-dichloropyridine

17 June, 2015 - 20:17

Org. Biomol. Chem., 2015, 13,6832-6838
DOI: 10.1039/C5OB00866B, PaperSebastian Reimann, Silvio Parpart, Peter Ehlers, Muhammad Sharif, Anke Spannenberg, Peter Langer
Chemoselective Suzuki-Miyaura reactions on 3,5-dibromo-2,6-dichloropyridine were studied.
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Synthesis of carbazoloquinone natural products 'on-water'

17 June, 2015 - 20:17

Org. Biomol. Chem., 2015, 13,6866-6878
DOI: 10.1039/C5OB00852B, PaperP. Norcott, C. S. P. McErlean
The total synthesis of a number of carbazolo-1,4-quinone natural products using on-water chemistry is described.
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CuX2-mediated oxybromination/aminochlorination of unsaturated amides: synthesis of iminolactones and lactams

17 June, 2015 - 20:17

Org. Biomol. Chem., 2015, 13,6690-6693
DOI: 10.1039/C5OB00520E, CommunicationZhi-Qiang Zhang, Feng Liu
A CuX2-mediated halocyclization of [gamma],[small delta]-unsaturated amides for the synthesis of functionalized iminolactones and lactams respectively is described.
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Glycosmisines A and B: isolation of two new carbazole-indole-type dimeric alkaloids from Glycosmis pentaphylla and an evaluation of their antiproliferative activities

17 June, 2015 - 20:17

Org. Biomol. Chem., 2015, 13,6773-6781
DOI: 10.1039/C5OB00695C, PaperYu Chen, Chu Tang, Yi Wu, Shasha Mo, Sha Wang, Guangzhong Yang, Zhinan Mei
Two unique carbazole-indole-type dimeric alkaloids, glycosmisines A (1) and B (2), have been isolated from the stems of Glycosmis pentaphylla and their structures are elucidated by 1D and 2D NMR analyses).
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4-(Dimethylamino)pyridine-catalysed iodolactonisation of [gamma],[small delta]-unsaturated carboxylic acids

17 June, 2015 - 20:17

Org. Biomol. Chem., 2015, 13,6766-6772
DOI: 10.1039/C5OB00806A, PaperChuisong Meng, Zhihui Liu, Yuxiu Liu, Qingmin Wang
4-(Dimethylamino)pyridine functioned as an excellent catalyst for iodolactonization reactions of [gamma],[small delta]-unsaturated carboxylic acids, affording [gamma]-lactones, [small delta]-lactones, or both.
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Fundamental reaction pathway and free energy profile of proteasome inhibition by syringolin A (SylA)

17 June, 2015 - 20:17

Org. Biomol. Chem., 2015, 13,6857-6865
DOI: 10.1039/C5OB00737B, PaperDonghui Wei, Mingsheng Tang, Chang-Guo Zhan
First-principles QM/MM-FE calculations led to understanding the detailed mechanism of the inhibition reaction of proteasome with SylA.
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Nickel-catalyzed synthesis of diarylsulfides and sulfones via C-H bond functionalization of arylamides

17 June, 2015 - 20:17

Org. Biomol. Chem., 2015, 13,6803-6813
DOI: 10.1039/C5OB00149H, PaperVutukuri Prakash Reddy, Renhua Qiu, Takanori Iwasaki, Nobuaki Kambe
The sulfenylation and sulfonylation of (sp2)C-H bonds of benzamides were achieved with the aid of a bidentate directing group.
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