1-Benzoyl-2-(2-nitrophenyl)-1H-benzimidazole derivatives: A novel approach to the development of new HIV-1 reverse transcriptase inhibitors

David Vásquez, Carlos F. Lagos, Jaime Mella-Raipán, Luis González, Roberto Ebensperger, M. Javiera Alvarez-Figueroa, Edmundo Sáez, Hernán Pessoa-Mahana, Raúl Araya-Secchp, Angel González-Wong, Tomás Pérez-Acle, C. David Pessoa-Mahana

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)1281-1287
Number of pages7
JournalJournal of the Chilean Chemical Society
Volume52
Issue number4
DOIs
Publication statusPublished - 2007

Keywords

  • Benzoylbenzimidazole derivatives
  • HIV-1 RT
  • Molecular modeling
  • NNRTIs

ASJC Scopus subject areas

  • Chemistry(all)

Fingerprint

Dive into the research topics of '1-Benzoyl-2-(2-nitrophenyl)-1H-benzimidazole derivatives: A novel approach to the development of new HIV-1 reverse transcriptase inhibitors'. Together they form a unique fingerprint.

Cite this