Royal Society of Chemistry

The direct electrophilic cyanation of [small beta]-keto esters and amides with cyano benziodoxole

Org. and Biomol. Chem. - 27 November, 2014 - 17:54

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02032D, CommunicationYao-Feng Wang, Jiashen Qiu, Dejie Kong, Yongtao Gao, Feipeng Lu, Pran Gopal Karmaker, Fu-Xue Chen
Electrophilic cyanating agent C1 accomplishes the direct cyanation of [small beta]-keto esters and amides without any catalyst and base.
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Quinoline-derived two-photon sensitive quadrupolar probes

Org. and Biomol. Chem. - 27 November, 2014 - 17:54

Org. Biomol. Chem., 2014, 12,9899-9908
DOI: 10.1039/C4OB01551G, PaperPetra Dunkel, Christine Tran, Thibault Gallavardin, Hamid Dhimane, David Ogden, Peter I. Dalko
Quadrupolar 8-dimethylaminoquinoline-derived photosensitive probes underwent photolysis under UV (365 nm) and NIR (730 nm two-photon (TP)) irradiation conditions.
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A facile approach to spirocyclic 2-azido indolines via azidation of indoles with ceric ammonium nitrate

Org. and Biomol. Chem. - 27 November, 2014 - 17:54

Org. Biomol. Chem., 2014, 12,9769-9772
DOI: 10.1039/C4OB01549E, CommunicationJing Li, Mao Liu, Qi Li, Hua Tian, Yian Shi
This paper describes azidation of indoles with NaN3 and ceric ammonium nitrate (CAN), giving a variety of spirocyclic 2-azido indolines in good yields and moderate diastereoselectivities.
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Enantioselective synthesis of [small alpha]-benzylated lanthionines and related tripeptides for biological incorporation into E. coli peptidoglycan

Org. and Biomol. Chem. - 27 November, 2014 - 17:54

Org. Biomol. Chem., 2014, 12,9853-9863
DOI: 10.1039/C4OB01476F, PaperThibaut Denoel, Astrid Zervosen, Christian Lemaire, Bernard Joris, Mireille Herve, Didier Blanot, Guillermo Zaragoza, Andre Luxen
The synthesis of modified tripeptides (S)-Ala-[gamma]-(R)-Glu-X, where X = (R,S) or (R,R) diastereomers of [small alpha]-benzyl or [small alpha]-(4-azidobenzyl)lanthionine, was carried out.
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Design and synthesis of a mitochondria-targeting carrier for small molecule drugs

Org. and Biomol. Chem. - 27 November, 2014 - 17:54

Org. Biomol. Chem., 2014, 12,9793-9796
DOI: 10.1039/C4OB01981D, CommunicationJunyan Han, Tae Hoon Lee, Ching-Hsuan Tung, Daniel Y. Lee
A novel mitochondria-targeting carrier QCy7HA was developed, which transported the covalently attached doxorubicin (DOX) to mitochondria specifically, resulting in the limitation of the effects of P-glycoprotein efflux pumps of multidrug-resistant cells on DOX.
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Highly efficient modular metal-free synthesis of 3-substituted 2-quinolones

Org. and Biomol. Chem. - 27 November, 2014 - 17:54

Org. Biomol. Chem., 2014, 12,9786-9788
DOI: 10.1039/C4OB02131B, CommunicationAlexander V. Aksenov, Alexander N. Smirnov, Nicolai A. Aksenov, Inna V. Aksenova, Asiyat S. Bijieva, Michael Rubin
A modular approach to 3-substituted 2-quinolones via a cascade annulation reaction between 4-nitroketones and hydrazines has been developed.
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Primary amino acid catalyzed asymmetric intramolecular Mannich reaction for the synthesis of 2-aryl-2,3-dihydro-4-quinolones

Org. and Biomol. Chem. - 27 November, 2014 - 17:54

Org. Biomol. Chem., 2014, 12,9789-9792
DOI: 10.1039/C4OB02146K, CommunicationBuddhadeb Mondal, Subhas Chandra Pan
A high enantioselective synthesis of 2-aryl-2,3-dihydro-4-quinolones has been developed via intramolecular Mannich reaction using primary amino acids as catalysts.
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A facile approach to tryptophan derivatives for the total synthesis of argyrin analogues

Org. and Biomol. Chem. - 27 November, 2014 - 17:54

Org. Biomol. Chem., 2014, 12,9764-9768
DOI: 10.1039/C4OB02107J, CommunicationOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Chou-Hsiung Chen, Sivaneswary Genapathy, Peter M. Fischer, Weng C. Chan
Utilising a chiral auxiliary-facilitated Strecker amino acid synthesis strategy, indole-substituted (S)-tryptophans have been obtained from corresponding indoles; the former in turn were used for the synthesis of a potent antibacterial agent, argyrin and its analogues.
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Synthesis of coenzyme A thioesters using methyl acyl phosphates in an aqueous medium

Org. and Biomol. Chem. - 27 November, 2014 - 17:54

Org. Biomol. Chem., 2014, 12,9760-9763
DOI: 10.1039/C4OB02079K, CommunicationMohan Pal, Stephen L. Bearne
Regioselective S-acylation of coenzyme A is achieved under aqueous conditions using various aliphatic and aromatic carboxylic acids activated as their methyl acyl phosphate monoesters.
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Anion carrier formation by calix[4]arene-bis-hydroxymethylphosphonic acid in bilayer membranes

Org. and Biomol. Chem. - 27 November, 2014 - 17:54

Org. Biomol. Chem., 2014, 12,9811-9821
DOI: 10.1039/C4OB01886A, PaperOleg Ya. Shatursky, Ludmila A. Kasatkina, Roman V. Rodik, Sergiy O. Cherenok, Alexander A. Shkrabak, Tatiana O. Veklich, Tatiana A. Borisova, Sergyi O. Kosterin, Vitaly I. Kalchenko
Calix[4]arene C-99-mediated ionic transport follows mobile carrier mode of facilitated diffusion (relative permeability PCl-/PK+ [similar] 3) with the passage of 20 ions per second.
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Sulfinate derivatives: dual and versatile partners in organic synthesis

Org. and Biomol. Chem. - 27 November, 2014 - 17:54

Org. Biomol. Chem., 2014, 12,9743-9759
DOI: 10.1039/C4OB01727G, Review ArticleJessy Aziz, Samir Messaoudi, Mouad Alami, Abdallah Hamze
Recent advances in the preparation and synthetic uses of sulfinic acids and their derivatives are highlighted in this review. They are used as versatile partners in sulfonylative and desulfitative reactions.
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Strained olefin enables triflic anhydride mediated direct dehydrative glycosylation

Org. and Biomol. Chem. - 27 November, 2014 - 17:54

Org. Biomol. Chem., 2014, 12,9781-9785
DOI: 10.1039/C4OB01807A, CommunicationGuohua Chen, Qiang Yin, Jian Yin, Xiangying Gu, Xiao Liu, Qidong You, Yue-Lei Chen, Bing Xiong, Jingkang Shen
Tf2O mediated dehydrative glycosylation was enabled by strained olefins, including beta-(-)-pinene, and inhibited by other typical bases.
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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. - 27 November, 2014 - 17:54

Org. Biomol. Chem., 2014, 12,9777-9780
DOI: 10.1039/C4OB02170C, CommunicationYongcheng Wu, Xiaopeng Peng, Bingling Luo, Fuhai Wu, Bo Liu, Fenyun Song, Peng Huang, Shijun Wen
As the tile reaction shows, an array of dibenzocarbazoles were obtained via dual C-H functionalization of indoles with cyclic diaryliodoniums in a single operation.
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Highly enantioselective reaction of 2-oxindoles with (3-indolyl)methanols by cooperative Catalysis of a Lewis acid and organocatalyst

Org. and Biomol. Chem. - 27 November, 2014 - 17:54

Org. Biomol. Chem., 2014, 12,9881-9886
DOI: 10.1039/C4OB02035A, PaperChuan-Li Ren, Tao Zhang, Xing-Yong Wang, Tao Wu, Jing Ma, Qing-Qing Xuan, Feng Wei, Hong-Yan Huang, Dong Wang, Li Liu
An efficient cooperative biscinchona alkaloid and Lewis acid catalytic system was developed in the enantioselective [small alpha]-alkylation of 2-oxindoles with (3-indolyl)(phenyl)methanols.
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Synthesis and biological evaluation of imidazo[1,5-a]pyridine-benzimidazole hybrids as inhibitors of both tubulin polymerization and PI3K/Akt pathway

Org. and Biomol. Chem. - 27 November, 2014 - 17:54

Org. Biomol. Chem., 2014, 12,9864-9880
DOI: 10.1039/C4OB01930J, PaperAhmed Kamal, A. V. Subba Rao, V. Lakshma Nayak, N. V. Subba Reddy, Konderu Swapna, G. Ramakrishna, Mallika Alvala
Imidazo[1,5-a]pyridine-benzimidazole hybrids are firstly reported herein to induce cytotoxicity by targeting microtubules.
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New insights into the structure-spectrum relationship in S65T/H148D and E222Q/H148D green fluorescent protein mutants: a theoretical assessment

Org. and Biomol. Chem. - 27 November, 2014 - 17:54

Org. Biomol. Chem., 2014, 12,9845-9852
DOI: 10.1039/C4OB01462F, PaperPau Armengol, Ricard Gelabert, Miquel Moreno, Jose M. Lluch
Dynamic simulations and excited state calculations track the origin of the absorption spectrum red-shift in two green fluorescent protein mutants.
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Base-switched annuloselectivity in the reactions of ethyl malonyl chloride and imines

Org. and Biomol. Chem. - 27 November, 2014 - 17:54

Org. Biomol. Chem., 2014, 12,9822-9830
DOI: 10.1039/C4OB01454E, PaperZhanhui Yang, Siqi Li, Zhong Zhang, Jiaxi Xu
The [2 + 2] and [2 + 2 + 2] annuloselectivity in the reactions of ethyl malonyl chloride with imines was controlled by different bases, providing a simple synthesis of [small beta]-lactam-3-carboxylates and 2,3-dihydro-1,3-oxazin-4-ones.
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An efficient synthetic route to 1,3-bis(arylethynyl)isobenzofuran using alkoxybenzocyclobutenone as a reactive platform

Org. and Biomol. Chem. - 27 November, 2014 - 17:54

Org. Biomol. Chem., 2014, 12,9773-9776
DOI: 10.1039/C4OB02012J, CommunicationKenta Asahina, Suguru Matsuoka, Ryosuke Nakayama, Toshiyuki Hamura
An efficient synthetic method of 1,3-bis(arylethynyl)isobenzofurans is developed.
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1-Trifluoromethylated isoquinolines via radical trifluoromethylation of isonitriles

Org. and Biomol. Chem. - 27 November, 2014 - 17:54

Org. Biomol. Chem., 2014, 12,9895-9898
DOI: 10.1039/C4OB02145B, PaperBo Zhang, Armido Studer
A simple and efficient approach to biologically important 1-trifluoroalkylated isoquinolines starting with readily prepared [small beta]-aryl-[small alpha]-isocyano-acrylates and Rf-I(III)-reagents (Rf = CF3, C2F5, C3F7) is described.
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Conformational equilibria in selected A-type trimeric procyanidins

Org. and Biomol. Chem. - 27 November, 2014 - 17:54

Org. Biomol. Chem., 2014, 12,9837-9844
DOI: 10.1039/C4OB02086C, PaperMarta K. Dudek (Jamroz), Slawomir Kazmierski, Kamil Stefaniak, Vitold B. Glinski, Jan. A. Glinski
There are two favored conformations of A-type procyanidin trimers: the (+[small phi])-rotamer and the (-[small phi]) one. Their ratio depends on the procyanidin structure and solvent - different solvents favor different conformers.
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