Royal Society of Chemistry

Sulfinate Derivatives: Dual and Versatile Partners in Organic Synthesis

Org. and Biomol. Chem. - 20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01727G, Review Articlejessy aziz, SAMIR MESSAOUDI, Mouad Alami, abdallah hamze
Sulfinic acids and their salts have recently emerged as versatile coupling partners to efficiently access a wide variety of hetero- and carbocyclic compounds, under relatively mild conditions. Their growing importance...
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Irriversible Covalent Modification of Type I Dehydroquinase by a Stable Schiff Base

Org. and Biomol. Chem. - 20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01782J, PaperLorena Tizon, Maria Maneiro, Antonio Peon, Jose Otero, Emilio Lence, Sergio Poza, Mark J. van Raaij, Paul Thompson, Alastair R. Hawkins, Concepcion Gonzalez-Bello
The irreversible inhibition of type I dehydroquinase (DHQ1), the third enzyme of the shikimic acid pathway, has been investigated by structural, biochemical and computational studies. Two epoxides, which are mimetics...
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Improved synthesis of the super antioxidant, ergothioneine and its biosynthetic pathway intermediates.

Org. and Biomol. Chem. - 20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02023E, PaperAnwar Jardine, Peguy Lutete Khonde
Ergothioneine along with mycothiol, are low molecular mass redox protective thiols present in Actinomycetes, in particular mycobacteria. We report the improved chemical synthesis of ergothioneine (ESH) and biosynthetic pathway intermediates...
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Synthesis and Antifungal Activity of 1,2,3-Triazole Phenylhydrazone Derivatives

Org. and Biomol. Chem. - 20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01758G, PaperZhicheng Dai, Yongfei Chen, Mao Zhang, Shengkun Li, Tingting Yang, Li Shen, Jianxin Wang, Shao-Song Qian, Hai-Liang Zhu, Yonghao Ye
A series of 1,2,3-triazole phenylhydrazone were designed and synthesized as antifungal agents. Their structures were determined based on 1H-NMR spectroscopy, MS, elemental analysis and X-ray single-crystal diffraction. The antifungal activities...
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Stereoselective Synthesis of 1,2-Diamine Containing Indolines by a Conjugate Addition Nitro-Mannich Reaction

Org. and Biomol. Chem. - 20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01793E, PaperJ C Anderson, Ian B Campbell, Sebastien Campos, Jonathan Shannon, D A Tocher
A conjugate addition nitro-Mannich reaction followed by nitro reduction and intramolecular N-arylation gives diastereomerically pure substituted 1,2-diamine containing indolines. Placing the N-arylation cyclisation handle on the imine precursor derived from...
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Strained Olefin Enables Triflic Anhydride Mediated Direct Dehydrative Glycosylation

Org. and Biomol. Chem. - 20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01807A, CommunicationGuohua Chen, Qiang Yin, jian yin, Xiangying Gu, Xiao Liu, Qidong You, Yue-Lei Chen, Bing Xiong, Jingkang Shen
For the first time, we demonstrated that the Tf2O mediated direct dehydrative glycosylation was possible simply with strained olefins, and other typical bases were inhibitors of this reaction. We optimized...
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Total Synthesis and Biological Evaluation of the Natural Product (-)-Cyclonerodiol, a New Inhibitor of IL-4 Signaling

Org. and Biomol. Chem. - 20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02021A, PaperJens Gerald Langhanki, Kristina Rudolph, Gerhard Erkel, Till Opatz
In a screening program of natural compounds from fungi, the known cyclopentanoid sesquiterpene (-)-cyclonerodiol was identified as a specific inhibitor of the IL-4 induced STAT6 signaling pathway (IC50 = 9.7...
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Chiral recognition with a benzofuran receptor which mimics an oxyanion hole

Org. and Biomol. Chem. - 20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01954G, PaperAngel L. Fuentes de Arriba, Angel Gomez Herrero, Omayra Hernandez Rubio, Laura Marcos Monleon, Luis Simon, Victoria Alcazar, Francisca Sanz, Joaquin Rodriguez Moran
A new chiral benzofuran receptor has been synthesized and its properties in the association of amino acid derivatives have been studied. X-ray structures were obtained and these corroborate the presence...
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Mixed non-covalent assemblies of ethynyl nile red and ethynyl pyrene along oligonucleotide templates

Org. and Biomol. Chem. - 20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01860E, PaperPhilipp Ensslen, Yannic Fritz, Hans-Achim Wagenknecht
Ethynyl pyrene and ethynyl nile red as modifications at the 5-position of 2'-deoxuridines self-assemble non-covalently and specifically along oligo-2'-deoxyadenosines as templates. Oligo-2'-deoxyadenosines of the lengths (dA)10 - (dA)20 are able...
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Aryl-Palladium-NHC complex: Efficient Phosphine-free Catalyst Precursors for the Carbonylation of Aryl Iodides with Amines or Alkynes

Org. and Biomol. Chem. - 20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01878H, PaperChunyan Zhang, Jianhua Liu, Chungu Xia
A series of aryl-palladium-NHC compounds were prepared according to the reported methods and their catalytic activity in the carbonylation of aryl iodides to synthesize [small alpha]-keto amides and alkynones were examined....
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Efficient Merging of Copper and Photoredox Catalysis for the Asymmetric Cross-Dehydrogenative-Coupling of Alkynes and Tetrahydroisoquinolines

Org. and Biomol. Chem. - 20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02138J, PaperInna Perepichka, Soumen Kundu, Zoe Hearne, Chao-Jun Li
A highly efficient catalytic asymmetric alkynylation of prochiral CH2 groups in tetrahydroisoquinoline was developed using copper catalyzed cross-dehydrogenative-coupling of sp3 and sp C-H bonds with the assistance of a photocatalyst...
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The Stability of Nitrogen-Centered Radicals

Org. and Biomol. Chem. - 20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01656D, PaperHendrik Zipse, Johnny Hioe, Valerije Vrcek, Davor Sakic
Radical stabilization energies (RSEs) for a wide variety of nitrogen-centered radicals and their protonated counterparts have been calculated at G3(MP2)-RAD and G3B3 level. The calculated RSE values can be rationalized...
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An efficient reagent for covalent introduction of alkyne into proteins

Org. and Biomol. Chem. - 20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01873G, CommunicationJie Zhang, Dejun Ma, Dawei Du, Zhen Xi, Long Yi
A cheap and bench-stable reagent was synthesized for direct and covalent introduction of alkynes into tyrosine of target proteins, which can be further modified based on click reaction to achieve...
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Silver(I)-Catalyzed Annulation for the Regioselective Synthesis of N-Imino-[gamma]-Carbolinium Ylides from Hydrazones of Indole-3-Carbonyl Derivatives and Propargylic Alcohols

Org. and Biomol. Chem. - 20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02020K, CommunicationZhuang-ping Zhan, Yu Zhu, Xin-Rui Shen, Hai-tao Tang, Min Lin
A regioselective efficient synthetic approach to N-imino-[gamma]-carbolinium ylides via AgOTf-catalyzed iminoannulation has been developed. This transformation proceeds via a silver(I) triflate-catalyzed consecutive Friedel-Crafts reaction/N-C bond formation sequence between readily available...
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Cationic azacryptands as selective three-way DNA junction binding agents

Org. and Biomol. Chem. - 20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01846J, PaperJana Novotna, Aurelien Laguerre, Anton Granzhan, Marc Pirrotta, Marie-Paule Teulade-Fichou, David Monchaud
DNA damaging agents are among the most powerful anticancer drugs currently under clinical use. As an alternative to irreversible nucleobase damages and DNA strand breaks, the non-covalent stabilization of unusual,...
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Palladium catalyzed dual C-H functionalization of indoles with cyclic diaryliodoniums, an approach to ring fused carbazole derivatives

Org. and Biomol. Chem. - 20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02170C, CommunicationYongcheng Wu, Xiaopeng Peng, Bingling Luo, Fu-Hai Wu, Bo Liu, Fen-Yun Song, Shijun Wen, Peng Huang
Palladium (Ⅱ)-catalyzed dual C-H functionalization of indoles with cyclic diaryliodoniums was successfully achieved, providing a concise method to synthesize dibenzocarbazoles. In one single operation, two C-C bonds and one ring...
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Corrin-based chemosensors for the ASSURED detection of endogenous cyanide

Org. and Biomol. Chem. - 20 October, 2014 - 09:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01889C, PerspectiveFelix Zelder, Lucas Tivana
Cassava (Manihot esculenta Crantz) is a staple food for more than 500 million people, especially in Africa and South America.
To cite this article before page numbers are assigned, use the DOI form of citation above.
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The Direct Electrophilic Cyanation of [small beta]-Keto Esters and Amides with Cyano Benziodoxole

Org. and Biomol. Chem. - 20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02032D, CommunicationYao-Feng Wang, Jiashen Qiu, Dejie Kong, Yongtao Gao, Feipeng Lu, Pran Gopal Karmaker, fuxue chen
The direct electrophilic [small alpha]-cyanation of [small beta]-keto esters and amides has been developed using hypervalent iodine benziodoxole-derived cyano reagent. It accomplishes within 10 min without any catalyst in DMF at room...
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Silver-Mediated Oxidative Vinylic C-H Bond Sulfenylation of Enamides with Disulfides

Org. and Biomol. Chem. - 20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01970A, CommunicationLuo Yang, Qing Wen, Fuhong Xiao, Guo-Jun Deng
A silver-mediated oxidative vinylic C-H bond sulfenylation of enamides was developed. This method is compatible with diaryl and dialkyl disulfides to deliver biological precious chalcogenated olefins efficiently. A plausible non-chain...
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QSAR Study on the Inhibition Mechanism of Matrix Metalloproteinase-12 by Arylsulfone Analogues Based on Molecular Orbital Calculations

Org. and Biomol. Chem. - 20 October, 2014 - 09:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01843E, PaperSeiji Hitaoka, Hiroshi Chuman, Kazunari Yoshizawa
A binding mechanism between human matrix metalloproteinase-12 (MMP-12) and eight arylsulfone analogs having two types of carboxylic and hydroxamic acids as the most representative zinc binding group is investigated by...
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