Conformation study of 2-arylbenzimidazoles as inhibitors of Chlamydia pneumoniae growth

Antti Siiskonen, Leena Keurulainen, Olli Salin, Paula Kiuru, Leena Pohjala, Pia Vuorela, Jari Yli-Kauhaluoma

Research output: Contribution to journalArticleScientificpeer-review

4 Citations (Scopus)

Abstract

Chlamydia pneumoniae is a worldwide cause of various respiratory track diseases ranging from asymptomatic pharyngeal infection to severe, sometimes fatal pneumonia. We have previously identified 2-arylbenzimidazoles as highly active antichlamydial compounds. In this work the importance of conformational effects on the structure-activity relationship of these compounds was studied. To simplify calculations, properly substituted N-phenylbenzamides, or the corresponding heterocyclic compounds, and 2-arylbenzimidazoles were used as model compounds. They were energy minimized and the energy differences between certain conformations were calculated. The main finding was that the compounds which can more easily adopt a non-planar conformation show higher bioactivity. This finding can be utilized in designing new derivatives or in constructing a pharmacophore model. (C) 2012 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)4882-4886
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume22
Issue number14
DOIs
Publication statusPublished - 15 Jul 2012
Externally publishedYes
Publication typeA1 Journal article-refereed

Keywords

  • Chlamydia pneumoniae
  • Conformational effects
  • Structure-activity relationship
  • 2-Arylbenzimidazoles
  • N-Phenylbenzamides
  • SEROLOGICAL EVIDENCE
  • TWAR
  • ASSOCIATION
  • INFECTION
  • DISEASE
  • DESIGN

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