Design, synthesis, structure-activity relationships, and molecular modeling studies of 2,3-diaryl-1,3-thiazolidin-4-ones as potent anti-HIV agents

  • J Med Chem. 2002 Nov 21;45(24):5410-3. doi: 10.1021/jm020977+.
Maria L Barreca  1 ,  Jan Balzarini ,  Alba Chimirri ,  Erik De Clercq ,  Laura De Luca ,  Hans Dieter Höltje ,  Monika Höltje ,  Anna Maria Monforte ,  Pietro Monforte ,  Christophe Pannecouque ,  Angela Rao ,  Maria Zappalà
Affiliations
  • 1. Dipartimento Farmaco-Chimico, Università di Messina, Viale Annunziata, 98168 Messina, Italy.
PMID: 12431069 DOI: 10.1021/jm020977+
Abstract

Starting from 1H,3H-thiazolo[3,4-a]benzimidazoles (TBZs), we performed the design, synthesis, and the structure-activity relationship studies of a series of 2,3-diaryl-1,3-thiazolidin-4-ones. Some derivatives proved to be highly effective in inhibiting HIV-1 replication at nanomolar concentrations with minimal cytotoxicity, thereby acting as nonnucleoside HIV-1 RT inhibitors (NNRTIs). Computational studies were used to delineate the ligand-RT interactions and to probe the binding of the ligands to HIV-1 RT.