Org. and Biomol. Chem.

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Investigation of the Passerini and Ugi reactions in [small beta]-lactam aldehydes. Synthetic applications

27 January, 2015 - 09:17

Org. Biomol. Chem., 2015, 13,1387-1394
DOI: 10.1039/C4OB02289K, PaperBenito Alcaide, Pedro Almendros, Cristina Aragoncillo, Ricardo Callejo, M. Pilar Ruiz, M. Rosario Torres
Ugi and Passerini multicomponent reactions on 4-oxoazetidine-2-carboxaldehydes allow the straightforward synthesis of highly functionalized [small beta]-lactams.
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Gd(OTf)3-catalyzed synthesis of geranyl esters for the intramolecular radical cyclization of their epoxides mediated by titanocene(III)

27 January, 2015 - 09:17

Org. Biomol. Chem., 2015, 13,1358-1366
DOI: 10.1039/C4OB02312A, PaperWilliam H. Garcia Santos, Carlos E. Puerto Galvis, Vladimir V. Kouznetsov
The catalytic activity of Gd(OTf)3 for the direct esterification of geraniol and the regio- and stereo-controlled radical cyclization of their epoxides mediated by titanocene(III) is described.
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A case of oxoanion recognition based on combined cationic and neutral C-H hydrogen bond interactions

27 January, 2015 - 09:17

Org. Biomol. Chem., 2015, 13,1339-1346
DOI: 10.1039/C4OB02288B, PaperFabiola Zapata, Paula Sabater, Antonio Caballero, Pedro Molina
A bidentate bis-(benzimidazolium) receptor containing pyrene as fluorescent signaling units recognizes sulphate and hydrogenpyrophosphate in a competitive water-DMSO medium through combinations of cationic and neutral C-H hydrogen bonding.
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Multi-substituted 8-aminoimidazo[1,2-a]pyrazines by Groebke-Blackburn-Bienayme reaction and their Hsp90 inhibitory activity

27 January, 2015 - 09:17

Org. Biomol. Chem., 2015, 13,1531-1535
DOI: 10.1039/C4OB01865F, PaperJing Ren, Min Yang, Hongchun Liu, Danyan Cao, Danqi Chen, Jian Li, Le Tang, Jianhua He, Yue-Lei Chen, Meiyu Geng, Bing Xiong, Jingkang Shen
Various 3,8-diaminoimidazo[1,2-a]pyrazines were efficiently prepared by MCR and some products showed moderate Hsp90 inhibitory activity.
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Synthesis and biological evaluation of novel pyrano[3,2-c]carbazole derivatives as anti-tumor agents inducing apoptosis via tubulin polymerization inhibition

27 January, 2015 - 09:17

Org. Biomol. Chem., 2015, 13,1404-1414
DOI: 10.1039/C4OB02015D, PaperPannala Padmaja, Garikapati Koteswara Rao, Adisherla Indrasena, Basireddy V. Subba Reddy, Nibedita Patel, Anver Basha Shaik, Narayana Reddy, Pramod K. Dubey, Manika Pal Bhadra
A series of novel pyrano[3,2-c]carbazole derivatives have been synthesized and antiproliferative activity of the derivatives were investigated on various cancer cell lines.
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Improved synthesis of the super antioxidant, ergothioneine, and its biosynthetic pathway intermediates

27 January, 2015 - 09:17

Org. Biomol. Chem., 2015, 13,1415-1419
DOI: 10.1039/C4OB02023E, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Peguy Lutete Khonde, Anwar Jardine
Ergothioneine and mycothiol are low molecular mass redox protective thiols present in actinomycetes, in particular mycobacteria.
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Efficient synthesis of [small alpha]- and [small delta]-carbolines by sequential Pd-catalyzed site-selective C-C and twofold C-N coupling reactions

27 January, 2015 - 09:17

Org. Biomol. Chem., 2015, 13,1375-1386
DOI: 10.1039/C4OB02226B, PaperTran Quang Hung, Tuan Thanh Dang, Julia Janke, Alexander Villinger, Peter Langer
Two concise and efficient approaches were developed for the synthesis of [small alpha]- and [small delta]-carboline derivatives.
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Copper(I)-promoted cycloalkylation-peroxidation of unactivated alkenes via sp3 C-H functionalisation

27 January, 2015 - 09:17

Org. Biomol. Chem., 2015, 13,1307-1312
DOI: 10.1039/C4OB01962H, CommunicationArghya Banerjee, Sourav Kumar Santra, Aniket Mishra, Nilufa Khatun, Bhisma K. Patel
A copper-promoted cycloalkylation-peroxidation strategy has been developed via a three-component reaction involving cycloalkanes, tert-butyl hydroperoxide and internal conjugated alkene.
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Diastereoselective desymmetrization of diarylphosphinous acid-borane amides under Birch reduction

15 January, 2015 - 06:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02440K, PaperMarek Stankevic
Birch reduction of symmetrical diarylphosphinous acid-borane amides possessing a chiral amido group, proceeds with diastereoselectivity up to 72%.
To cite this article before page numbers are assigned, use the DOI form of citation above.
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Highly selective and sensitive detection of glutathione using mesoporous silica nanoparticles capped with disulfide-containing oligo(ethylene glycol) chains

13 January, 2015 - 05:54

Org. Biomol. Chem., 2015, 13,1017-1021
DOI: 10.1039/C4OB02083A, CommunicationSameh El Sayed, Cristina Gimenez, Elena Aznar, Ramon Martinez-Manez, Felix Sancenon, Maurizio Licchelli
Mesoporous silica nanoparticles loaded with safranin O and capped with disulfide-containing oligo(ethylene glycol) chains were used for the selective and sensitive fluorimetric detection of GSH.
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A chiral borane catalyzed asymmetric hydrosilylation of imines

13 January, 2015 - 05:54

Org. Biomol. Chem., 2015, 13,1013-1016
DOI: 10.1039/C4OB02419B, CommunicationXiaxia Zhu, Haifeng Du
An enantioselective hydrosilylation of imines was achieved using an in situ generated chiral borane to furnish amines with up to 82% ee.
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Water-soluble aryl-extended calix[4]pyrroles with unperturbed aromatic cavities: synthesis and binding studies

13 January, 2015 - 05:54

Org. Biomol. Chem., 2015, 13,1022-1029
DOI: 10.1039/C4OB02108H, PaperD. Hernandez-Alonso, S. Zankowski, L. Adriaenssens, P. Ballester
An aryl-extended calix[4]pyrrole receptor with four carboxylic groups at the lower rim binds N-oxides in water with high stability constants.
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Investigation of end processing and degradation of premature tRNAs and their application to stabilization of in vitro transcripts in wheat germ extract

13 January, 2015 - 05:54

Org. Biomol. Chem., 2015, 13,1008-1012
DOI: 10.1039/C4OB02221A, CommunicationAtsushi Ogawa, Yasunori Doi
We investigated the end processing and degradation of premature tRNAs in wheat germ extract (left), which led to the findings of end protectors for efficiently stabilizing an in vitro transcript (purple, right).
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Developing piperine towards TRPV1 and GABAA receptor ligands - synthesis of piperine analogs via Heck-coupling of conjugated dienes

13 January, 2015 - 05:54

Org. Biomol. Chem., 2015, 13,990-994
DOI: 10.1039/C4OB02242D, CommunicationLaurin Wimmer, David Schonbauer, Peter Pakfeifer, Angela Schoffmann, Sophia Khom, Steffen Hering, Marko D. Mihovilovic
Synthetic analogs of piperine, the pungent alkaloid of black pepper, were identified as selective ligands for either GABAA or TRPV1 receptors.
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An expedient approach to 1,2-dihydroisoquinoline derivatives via cobalt catalysed 6-endo dig cyclization followed by Mannich condensation of o-alkynylarylaldimines

13 January, 2015 - 05:54

Org. Biomol. Chem., 2015, 13,1000-1007
DOI: 10.1039/C4OB02036G, Communication Urvashi, Gaurav K. Rastogi, Sandeep K. Ginotra, Alka Agarwal, Vibha Tandon
A highly effective 6-endo dig cyclisation of o-alkynyl aldimines to 1,2-dihydroisoquinolines has been described via direct and nitro Mannich condensation using inexpensive and readily available cobalt chloride as catalyst.
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Ruthenium-catalyzed direct C3 alkylation of indoles with [small alpha],[small beta]-unsaturated ketones

13 January, 2015 - 05:54

Org. Biomol. Chem., 2015, 13,1254-1263
DOI: 10.1039/C4OB02124J, PaperShuai-Shuai Li, Hui Lin, Xiao-Mei Zhang, Lin Dong
In this paper, a simple and highly efficient ruthenium-catalyzed direct C3 alkylation of indoles with various [small alpha],[small beta]-unsaturated ketones without chelation assistance has been developed.
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Palladium-catalyzed oxidative cross-coupling of azole-4-carboxylates with indoles: an approach to the synthesis of pimprinine

13 January, 2015 - 05:54

Org. Biomol. Chem., 2015, 13,1243-1248
DOI: 10.1039/C4OB01844C, PaperHaipin Zhou, Kuo Gai, Aijun Lin, Jinyi Xu, Xiaoming Wu, Hequan Yao
A palladium-catalyzed oxidative cross-coupling reaction between azole-4-carboxylates and indoles forming 5-(3-indolyl)azoles with excellent regioselectivity has been developed.
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Tunneling in tocopherol-mediated peroxidation of 7-dehydrocholesterol

13 January, 2015 - 05:54

Org. Biomol. Chem., 2015, 13,1249-1253
DOI: 10.1039/C4OB02377C, PaperH. Muchalski, L. Xu, N. A. Porter
We report here that H-atom tunneling facilitates the propagation step in the tocopherol-mediated peroxidation (TMP) of 7-dehydrocholesterol. This process likely becomes a major propagation pathway when radical intermediates are isolated in cellular organelles or lipid particles such as low-density lipoproteins. In TMP of 7-DHC and deuterium-reinforced 7-DHC, the KIE of removing hydrogen/deuterium at C9 was found to be 21 +/- 1.
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Metal-catalyzed formation of 1,3-cyclohexadienes: a catalyst-dependent reaction

13 January, 2015 - 05:54

Org. Biomol. Chem., 2015, 13,1225-1233
DOI: 10.1039/C4OB01922A, PaperShifa Zhu, Xiaobing Huang, Tian-Qi Zhao, Tongmei Ma, Huanfeng Jiang
A metal-dependent and complementary catalytic method to synthesize the cyclohexadienes has been developed. When gold or indium salts were used as catalysts, 1,3-cyclohexadiene (1,3-CHD) could be obtained; when Cu(OTf)2 was used as the catalyst, however, another isomer 2,4-cyclohexadiene (2,4-CHD) was furnished instead.
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Fluorescent organic nanoparticles of dihydropyrimidone derivatives for selective recognition of iodide using a displacement assay: application of the sensors in water and biological fluids

13 January, 2015 - 05:54

Org. Biomol. Chem., 2015, 13,1204-1212
DOI: 10.1039/C4OB02152E, PaperAmanpreet Kaur, Tilak Raj, Simanpreet Kaur, Narinder Singh, Navneet Kaur
Fluorescent organic nanoparticles (FON's) derived from dihydropyrimidone derivatives (1-4) were developed and evaluated for their sensor properties.
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