Novel indazole non-nucleoside reverse transcriptase inhibitors using molecular hybridization based on crystallographic overlays

J Med Chem. 2009 Feb 26;52(4):1219-23. doi: 10.1021/jm801322h.

Abstract

A major problem associated with non-nucleoside reverse transcriptase inhibitors (NNRTIs) for the treatment of HIV is their lack of resilience to mutations in the reverse transcriptase (RT) enzyme. Using structural overlays of the known inhibitors efavirenz and capravirine complexed in RT as a starting point, and structure-based drug design techniques, we have created a novel series of indazole NNRTIs that possess excellent metabolic stability and mutant resilience.

MeSH terms

  • Alkynes
  • Anti-HIV Agents / chemistry*
  • Anti-HIV Agents / pharmacology
  • Benzoxazines / pharmacology
  • Crystallography, X-Ray
  • Cyclopropanes
  • Drug Design
  • Drug Resistance, Viral / drug effects
  • Drug Resistance, Viral / genetics
  • Drug Stability
  • HIV / drug effects
  • HIV / enzymology
  • HIV / genetics
  • HIV Reverse Transcriptase / antagonists & inhibitors
  • HIV Reverse Transcriptase / genetics
  • Humans
  • Imidazoles / pharmacology
  • Indazoles / chemistry*
  • Indazoles / pharmacology
  • Molecular Structure
  • Mutation
  • Reverse Transcriptase Inhibitors / chemistry*
  • Reverse Transcriptase Inhibitors / pharmacology
  • Structure-Activity Relationship
  • Sulfur Compounds / pharmacology

Substances

  • Alkynes
  • Anti-HIV Agents
  • Benzoxazines
  • Cyclopropanes
  • Imidazoles
  • Indazoles
  • Reverse Transcriptase Inhibitors
  • Sulfur Compounds
  • reverse transcriptase, Human immunodeficiency virus 1
  • HIV Reverse Transcriptase
  • efavirenz
  • capravirine