The use of oxadiazole and triazole substituted naphthyridines as HIV-1 integrase inhibitors. Part 1: Establishing the pharmacophore

Bioorg Med Chem Lett. 2009 Mar 15;19(6):1802-6. doi: 10.1016/j.bmcl.2009.01.090. Epub 2009 Jan 30.

Abstract

A series of HIV-1 integrase inhibitors containing a novel metal binding motif consisting of the 8-hydroxy-1,6-naphthyridine core and either an oxadiazole or triazole has been identified. The design of the key structural components was based on a two-metal coordination pharmacophore. This report presents initial structure-activity data that shows the new chelation architecture delivers potent inhibition in both enzymatic and antiviral assays.

MeSH terms

  • Amino Acid Motifs
  • Anti-HIV Agents / chemical synthesis*
  • Anti-HIV Agents / pharmacology
  • Chelating Agents / pharmacology
  • Chemistry, Pharmaceutical / methods*
  • Drug Design
  • HIV Infections / drug therapy
  • HIV Integrase Inhibitors / chemical synthesis*
  • HIV Integrase Inhibitors / pharmacology
  • Humans
  • Models, Chemical
  • Molecular Structure
  • Naphthyridines / chemical synthesis*
  • Naphthyridines / pharmacology
  • Oxadiazoles / chemistry*
  • Structure-Activity Relationship
  • Triazoles / chemistry*
  • Virus Replication / drug effects
  • Virus Replication / genetics

Substances

  • Anti-HIV Agents
  • Chelating Agents
  • HIV Integrase Inhibitors
  • Naphthyridines
  • Oxadiazoles
  • Triazoles