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Facile synthesis of 4- and 7-azaindoles from the corresponding imines by palladium-catalyzed cascade C-C and C-N coupling

Org. and Biomol. Chem. - 24 May, 2015 - 14:17

Org. Biomol. Chem., 2015, 13,6047-6058
DOI: 10.1039/C5OB00720H, PaperNgo Nghia Pham, Thanh Tuan Dang, Ngoc Thang Ngo, Alexander Villinger, Peter Ehlers, Peter Langer
The cyclization of 2,3-dihalopyridines with readily available imines provides a convenient and regioselective approach to 4- and 7-azaindoles.
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Ring size in cyclic endomorphin-2 analogs modulates receptor binding affinity and selectivity

Org. and Biomol. Chem. - 24 May, 2015 - 14:17

Org. Biomol. Chem., 2015, 13,6039-6046
DOI: 10.1039/C5OB00565E, PaperJustyna Piekielna, Alicja Kluczyk, Luca Gentilucci, Maria Camilla Cerlesi, Girolamo Calo', Csaba Tomboly, Krzysztof Lapinski, Tomasz Janecki, Anna Janecka
A series of endomorphin-2 cyclic analogs with 17- to 14-membered rings was synthesized and evaluated in terms of opioid affinity and selectivity. Conformational studies enabled us to rationalize biological results.
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Binding of pixantrone to DNA at CpA dinucleotide sequences and bulge structures

Org. and Biomol. Chem. - 24 May, 2015 - 14:17

Org. Biomol. Chem., 2015, 13,5972-5982
DOI: 10.1039/C5OB00526D, PaperShyam K. Konda, Haiqiang Wang, Suzanne M. Cutts, Don R. Phillips, J. Grant Collins
The anti-cancer drug pixantrone intercalates predominantly from the minor groove at adenine bulge sites, but with approximately equal frequency from the minor and major grooves at CpA sites.
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Thiocyanation of BODIPY dyes and their conversion to thioalkylated derivatives

Org. and Biomol. Chem. - 24 May, 2015 - 14:17

Org. Biomol. Chem., 2015, 13,6031-6038
DOI: 10.1039/C5OB00499C, PaperLucas Cunha Dias de Rezende, Shaiani Maria Gil de Melo, Stijn Boodts, Bram Verbelen, Wim Dehaen, Flavio da Silva Emery
Thiocyanation and formation of thioalkylated BODIPYs is a simple and reliable way for their chemical modification and photophysical tuning.
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Hydroxyethylene isosteres introduced in type II collagen fragments substantially alter the structure and dynamics of class II MHC Aq/glycopeptide complexes

Org. and Biomol. Chem. - 24 May, 2015 - 14:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB00395D, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Cecilia Lindgren, Ida E. Andersson, Lotta Berg, Doreen Dobritzsch, Changrong Ge, Sabrina Haag, Urszula Uciechowska, Rikard Holmdahl, Jan Kihlberg, Anna Linusson
Introduction of hydroxyethylene isosteres into glycopeptides led to loss of Aq affinity and subsequent T cell response due to disruption of hydrogen bond networks.
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A mechanistic investigation of anti-elimination in (Z)-1,2-bis(arylseleno)-1-alkenes and their sulfur analogs

Org. and Biomol. Chem. - 24 May, 2015 - 14:17

Org. Biomol. Chem., 2015, 13,5964-5971
DOI: 10.1039/C5OB00490J, PaperAsami Tarao, Yukako Tabuchi, Eri Sugimoto, Miki Ikeda, Hitomi Uchimoto, Kenji Arimitsu, Hiroyuki Kimura, Ikuo Kawasaki, Masatoshi Kawahata, Kentaro Yamaguchi, Kiyoharu Nishide
Selenoxide anti-elimination in (Z)-1,2-bis(arylseleninyl)-1-alkenes is induced by the SeO interaction, whereas the sulfur analogs lacks this type of nonbonding interaction.
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Synthesis of multiply substituted 1,6-dihydropyridines through Cu(I)-catalyzed 6-endo cyclization

Org. and Biomol. Chem. - 24 May, 2015 - 14:17

Org. Biomol. Chem., 2015, 13,5955-5963
DOI: 10.1039/C5OB00356C, PaperHaruki Mizoguchi, Ryo Watanabe, Shintaro Minami, Hideaki Oikawa, Hiroki Oguri
Copper-catalyzed 6-endo cyclization of N-propargylic [small beta]-enaminocarbonyls was developed for the synthesis of oxidation-labile 1,6-dihydropyridines.
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An improved transition-metal-free synthesis of aryl alkynyl sulfides via substitution of a halide at an sp-centre

Org. and Biomol. Chem. - 24 May, 2015 - 14:17

Org. Biomol. Chem., 2015, 13,5859-5861
DOI: 10.1039/C5OB00494B, CommunicationRoomi Mohima Chowdhury, Jonathan D. Wilden
A simple high-yielding preparation of aryl alkynyl sulfides is presented. The reaction of a chloroacetylene with a thiolate salt in the presence of an amine mediator (dimethylamine or N,N[prime or minute]-dimethylethylenediamine) yields the alkynyl sulfides in excellent yields. The alkynyl chloride is easily prepared from the parent alkyne.
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Targeting intracellular bacteria with an extended cationic amphiphilic polyproline helix

Org. and Biomol. Chem. - 24 May, 2015 - 14:17

Org. Biomol. Chem., 2015, 13,5930-5936
DOI: 10.1039/C5OB00227C, PaperManish Nepal, Shankar Thangamani, Mohamed N. Seleem, Jean Chmielewski
Eradicating pathogenic bacteria that reside within mammalian cells is currently quite difficult. Herein we describe an agent with the dual properties of efficient mammalian cell penetration and potent antibacterial activity. Significantly, these activities can be combined to target pathogenic bacteria within macrophages.
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Cu-catalyzed debrominative cyanation of gem-dibromoolefins: a facile access to [small alpha],[small beta]-unsaturated nitriles

Org. and Biomol. Chem. - 24 May, 2015 - 14:17

Org. Biomol. Chem., 2015, 13,5918-5923
DOI: 10.1039/C5OB00394F, PaperBrij Bhushan Ahuja, Arumugam Sudalai
An efficient catalytic route for the synthesis of [small alpha],[small beta]-unsaturated nitriles from easily accessible gem-dibromoolefins has been developed.
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Rhenium-catalyzed dehydrogenative olefination of C(sp3)-H bonds with hypervalent iodine(III) reagents

Org. and Biomol. Chem. - 24 May, 2015 - 14:17

Org. Biomol. Chem., 2015, 13,5880-5884
DOI: 10.1039/C5OB00619H, CommunicationHaidong Gu, Congyang Wang
A dehydrogenative olefination of C(sp3)-H bonds is developed by merging rhenium catalysis with an alanine-derived hypervalent iodine(III) reagent.
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A lactone-fused cyclohexadiene as a versatile platform for diversified synthesis of 5,6,5-tricyclic scaffolds

Org. and Biomol. Chem. - 24 May, 2015 - 14:17

Org. Biomol. Chem., 2015, 13,5862-5866
DOI: 10.1039/C5OB00729A, CommunicationM. Shibuya, T. Sudoh, T. Kawamura, Y. Yamamoto
A new lactone-fused cyclohexadiene platform for the stereoselective synthesis of differently functionalized 5,6,5-tricyclic scaffolds.
The content of this RSS Feed (c) The Royal Society of Chemistry

Gold-catalyzed cascade C-H/C-H cross-coupling/cyclization/alkynylation: an efficient access to 3-alkynylpyrroles

Org. and Biomol. Chem. - 24 May, 2015 - 14:17

Org. Biomol. Chem., 2015, 13,5867-5870
DOI: 10.1039/C5OB00599J, CommunicationShuai Zhang, Yuanhong Ma, Jingbo Lan, Feijie Song, Jingsong You
An efficient approach to 3-alkynylpyrroles has been developed through the gold-catalyzed cascade oxidative C-H/C-H cross-coupling, cyclization and in situ oxidative alkynylation.
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The synthesis of new amphiphilic p-tert-butylthiacalix[4]arenes containing peptide fragments and their interaction with DNA

Org. and Biomol. Chem. - 24 May, 2015 - 14:17

Org. Biomol. Chem., 2015, 13,5894-5904
DOI: 10.1039/C5OB00548E, PaperPavel L. Padnya, Elena A. Andreyko, Olga A. Mostovaya, Ildar Kh. Rizvanov, Ivan I. Stoikov
The synthesis of new amphiphilic p-tert-butylthiacalix[4]arenes containing peptide fragments and their interaction with DNA is reported.
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77Se and 125Te NMR spectroscopy on a selectivity study of organochalcogenanes with L-amino acids

Org. and Biomol. Chem. - 24 May, 2015 - 14:17

Org. Biomol. Chem., 2015, 13,5924-5929
DOI: 10.1039/C5OB00373C, PaperMarcio S. Silva, Leandro H. Andrade
Organochalcogenanes exhibited a remarkably high selectivity for L-cysteine which was monitored by 77Se and 125Te NMR spectroscopy.
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Copper(II)-catalyzed highly regio- and stereo-selective hydrosilylation of unactivated internal alkynes with silylborate in water

Org. and Biomol. Chem. - 24 May, 2015 - 14:17

Org. Biomol. Chem., 2015, 13,5871-5874
DOI: 10.1039/C5OB00694E, CommunicationQing-Qing Xuan, Chuan-Li Ren, Li Liu, Dong Wang, Chao-Jun Li
The hydrosilylation of internal alkynes with Me2PhSiBpin catalyzed by Cu(OTf)2 in water provided multisubstituted vinylsilanes in high regio- and stereoselectivities.
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Divergent synthesis of 4,6-diarylated pyridin-2(1H)-ones from chalcones: novel access to 2,4,6-triaryl pyridines

Org. and Biomol. Chem. - 24 May, 2015 - 14:17

Org. Biomol. Chem., 2015, 13,5944-5954
DOI: 10.1039/C5OB00545K, PaperRajni Khajuria, Prakash Kannaboina, Kamal K. Kapoor, Annah Gupta, Gaurav Raina, Amanpreet Kaur Jassal, Love Karan Rana, Maninder S. Hundal, Parthasarathi Das
A wide range of 4,6-diarylated-2(1H)-one derivatives were synthesized in excellent yields from chalcones in one pot. Further the designed 4,6-diarylated pyridin-2(1H)-one derivatives have been successfully utilized in synthesizing 2,4,6-triarylpyridines.
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Stereo-controlled synthesis of polyheterocycles via the diene-transmissive hetero-Diels-Alder reaction of [small beta],[gamma]-unsaturated [small alpha]-keto esters

Org. and Biomol. Chem. - 24 May, 2015 - 14:17

Org. Biomol. Chem., 2015, 13,5875-5879
DOI: 10.1039/C5OB00503E, CommunicationTakashi Otani, Yumiko Tamai, Kazunori Seki, Tomohiro Kikuchi, Taiichiro Miyazawa, Takao Saito
Stereocontrolled synthesis of polyheterocycles via the diene-transmissive hetero Diels-Alder reaction of [small beta],[small chi]-unsaturated [small alpha]-keto esters is described.
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Convenient synthesis of functionalized spiro[indoline-3,2[prime or minute]-pyrrolizines] or spiro[indoline-3,3[prime or minute]-pyrrolidines] via multicomponent reactions

Org. and Biomol. Chem. - 24 May, 2015 - 14:17

Org. Biomol. Chem., 2015, 13,5905-5917
DOI: 10.1039/C5OB00437C, PaperJing Sun, Liang Chen, Hui Gong, Chao-Guo Yan
Multicomponent reactions of [small alpha]-amino acids, dialkyl acetylenedicarboxylates and 3-methyleneoxindoles afforded diverse functionalized spiro[indoline-3,2[prime or minute]-pyrrolizines], spiro[indoline-3,3[prime or minute]-pyrrolidines] and spiro[indoline-3,6[prime or minute]-pyrrolo[1,2-c]thiazoles].
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Synthesis, structural characterization and biological activity of two diastereomeric JA-Ile macrolactones

Org. and Biomol. Chem. - 24 May, 2015 - 14:17

Org. Biomol. Chem., 2015, 13,5885-5893
DOI: 10.1039/C5OB00362H, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Guillermo H. Jimenez-Aleman, Ricardo A. R. Machado, Helmar Gorls, Ian T. Baldwin, Wilhelm Boland
The synthesis and biological activity of two diastereomeric macrolactones derived from the partially inactive jasmonate 12-OH-JA-Ile are discussed. Both diastereoisomers induce nicotine production similar to methyl jasmonate in Nicotiana attenuata plants.
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