1-BENZOYL-2-(2-NITROPHENYL)-1H-BENZIMIDAZOLE DERIVATIVES: A NOVEL APPROACH TO THE DEVELOPMENT OF NEW HIV-1 REVERSE TRANSCRIPTASE INHIBITORS

A novel approach to the development of a new class of HIV-1 RT inhibitors is reported. The 1-benzoyl-2-aryl-1H-benzimidazole series was designed as a combination of two previously reported active scaffolds, the benzimidazole and benzoyl moieties. The active compounds of the series effectively blocke...

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Autores principales:	VÁSQUEZ,DAVID, LAGOS,CARLOS F, MELLA-RAIPÁN,JAIME, GONZÁLEZ,LUIS, EBENSPERGER,ROBERTO, ALVAREZ-FIGUEROA,M. JAVIERA, SÁEZ,EDMUNDO, PESSOA-MAHANA,HERNÁN, ARAYA-SECCHP,RAÚL, GONZÁLEZ-WONG,ANGEL, PÉREZ-ACLE,TOMÁS, PESSOA-MAHANA,C. DAVID
Lenguaje:	English
Publicado:	Sociedad Chilena de Química 2007
Materias:	NNRTIs HIV-1 RT molecular modeling benzoylbenzimidazole derivatives
Acceso en línea:	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072007000400002
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spelling	oai:scielo:S0717-970720070004000022008-04-301-BENZOYL-2-(2-NITROPHENYL)-1H-BENZIMIDAZOLE DERIVATIVES: A NOVEL APPROACH TO THE DEVELOPMENT OF NEW HIV-1 REVERSE TRANSCRIPTASE INHIBITORSVÁSQUEZ,DAVIDLAGOS,CARLOS FMELLA-RAIPÁN,JAIMEGONZÁLEZ,LUISEBENSPERGER,ROBERTOALVAREZ-FIGUEROA,M. JAVIERASÁEZ,EDMUNDOPESSOA-MAHANA,HERNÁNARAYA-SECCHP,RAÚLGONZÁLEZ-WONG,ANGELPÉREZ-ACLE,TOMÁSPESSOA-MAHANA,C. DAVID NNRTIs HIV-1 RT molecular modeling benzoylbenzimidazole derivatives A novel approach to the development of a new class of HIV-1 RT inhibitors is reported. The 1-benzoyl-2-aryl-1H-benzimidazole series was designed as a combination of two previously reported active scaffolds, the benzimidazole and benzoyl moieties. The active compounds of the series effectively blocked the reverse transcription in the micromolar range in an in vitro assay containing the wild-type enzyme. We have demonstrated that the 2-nitrophenyl C-2 substituent is an important structural feature for the desired biological activity in this series. Molecular docking experiments suggest that the active compounds adopt a butterflylike conformation within the binding pocket of the enzyme, with the benzoyl moiety located in an extended hydrophobic region defined mainly by Tyrl 81, Tyrl 88, and Trp229info:eu-repo/semantics/openAccessSociedad Chilena de QuímicaJournal of the Chilean Chemical Society v.52 n.4 20072007-01-01text/htmlhttp://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072007000400002en10.4067/S0717-97072007000400002
institution	Scielo Chile
collection	Scielo Chile
language	English
topic	NNRTIs HIV-1 RT molecular modeling benzoylbenzimidazole derivatives
spellingShingle	NNRTIs HIV-1 RT molecular modeling benzoylbenzimidazole derivatives VÁSQUEZ,DAVID LAGOS,CARLOS F MELLA-RAIPÁN,JAIME GONZÁLEZ,LUIS EBENSPERGER,ROBERTO ALVAREZ-FIGUEROA,M. JAVIERA SÁEZ,EDMUNDO PESSOA-MAHANA,HERNÁN ARAYA-SECCHP,RAÚL GONZÁLEZ-WONG,ANGEL PÉREZ-ACLE,TOMÁS PESSOA-MAHANA,C. DAVID 1-BENZOYL-2-(2-NITROPHENYL)-1H-BENZIMIDAZOLE DERIVATIVES: A NOVEL APPROACH TO THE DEVELOPMENT OF NEW HIV-1 REVERSE TRANSCRIPTASE INHIBITORS
description	A novel approach to the development of a new class of HIV-1 RT inhibitors is reported. The 1-benzoyl-2-aryl-1H-benzimidazole series was designed as a combination of two previously reported active scaffolds, the benzimidazole and benzoyl moieties. The active compounds of the series effectively blocked the reverse transcription in the micromolar range in an in vitro assay containing the wild-type enzyme. We have demonstrated that the 2-nitrophenyl C-2 substituent is an important structural feature for the desired biological activity in this series. Molecular docking experiments suggest that the active compounds adopt a butterflylike conformation within the binding pocket of the enzyme, with the benzoyl moiety located in an extended hydrophobic region defined mainly by Tyrl 81, Tyrl 88, and Trp229
author	VÁSQUEZ,DAVID LAGOS,CARLOS F MELLA-RAIPÁN,JAIME GONZÁLEZ,LUIS EBENSPERGER,ROBERTO ALVAREZ-FIGUEROA,M. JAVIERA SÁEZ,EDMUNDO PESSOA-MAHANA,HERNÁN ARAYA-SECCHP,RAÚL GONZÁLEZ-WONG,ANGEL PÉREZ-ACLE,TOMÁS PESSOA-MAHANA,C. DAVID
author_facet	VÁSQUEZ,DAVID LAGOS,CARLOS F MELLA-RAIPÁN,JAIME GONZÁLEZ,LUIS EBENSPERGER,ROBERTO ALVAREZ-FIGUEROA,M. JAVIERA SÁEZ,EDMUNDO PESSOA-MAHANA,HERNÁN ARAYA-SECCHP,RAÚL GONZÁLEZ-WONG,ANGEL PÉREZ-ACLE,TOMÁS PESSOA-MAHANA,C. DAVID
author_sort	VÁSQUEZ,DAVID
title	1-BENZOYL-2-(2-NITROPHENYL)-1H-BENZIMIDAZOLE DERIVATIVES: A NOVEL APPROACH TO THE DEVELOPMENT OF NEW HIV-1 REVERSE TRANSCRIPTASE INHIBITORS
title_short	1-BENZOYL-2-(2-NITROPHENYL)-1H-BENZIMIDAZOLE DERIVATIVES: A NOVEL APPROACH TO THE DEVELOPMENT OF NEW HIV-1 REVERSE TRANSCRIPTASE INHIBITORS
title_full	1-BENZOYL-2-(2-NITROPHENYL)-1H-BENZIMIDAZOLE DERIVATIVES: A NOVEL APPROACH TO THE DEVELOPMENT OF NEW HIV-1 REVERSE TRANSCRIPTASE INHIBITORS
title_fullStr	1-BENZOYL-2-(2-NITROPHENYL)-1H-BENZIMIDAZOLE DERIVATIVES: A NOVEL APPROACH TO THE DEVELOPMENT OF NEW HIV-1 REVERSE TRANSCRIPTASE INHIBITORS
title_full_unstemmed	1-BENZOYL-2-(2-NITROPHENYL)-1H-BENZIMIDAZOLE DERIVATIVES: A NOVEL APPROACH TO THE DEVELOPMENT OF NEW HIV-1 REVERSE TRANSCRIPTASE INHIBITORS
title_sort	1-benzoyl-2-(2-nitrophenyl)-1h-benzimidazole derivatives: a novel approach to the development of new hiv-1 reverse transcriptase inhibitors
publisher	Sociedad Chilena de Química
publishDate	2007
url	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072007000400002
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1-BENZOYL-2-(2-NITROPHENYL)-1H-BENZIMIDAZOLE DERIVATIVES: A NOVEL APPROACH TO THE DEVELOPMENT OF NEW HIV-1 REVERSE TRANSCRIPTASE INHIBITORS

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