Synthesis and HIV-1 reverse transcriptase inhibitor activity of some 2,5,6-substituted benzoxazole, benzimidazole, benzothiazole and oxazolo(4,5-b)pyridine derivatives

Arzneimittelforschung. 2003;53(4):266-71. doi: 10.1055/s-0031-1297107.

Abstract

In this study, the synthesis of some benzoxazoles and their analogues were described and their antiviral activities were studied together with the previously synthesized 2,5,6-trisubstituted benzoxazole, benzothiazole, benzimidazole and oxazolo(4,5-b)pyridine derivatives. The reverse transcriptase (RT) inhibitory activity of these compounds was determined using a commercial kit and assay system which utilizes the scintillation proximity assay principle. The results are concentration at which the compound inhibits RT activity by 50%). The compounds inhibited the in vitro binding of thymidine to the RT enzyme exhibiting IC50 values between 6.3 x 10(5) mumol/l-0.34 mumol/l and their activities were compared to some standard drugs such as 3'-azido-2',3'-dideoxythymidine triphosphate and dideoxythymidine triphosphate.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzimidazoles / chemical synthesis*
  • Benzimidazoles / pharmacology*
  • Benzoxazoles / chemical synthesis*
  • Benzoxazoles / pharmacology*
  • Dideoxynucleotides
  • HIV Reverse Transcriptase / antagonists & inhibitors*
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Pyridines / chemical synthesis*
  • Pyridines / pharmacology*
  • Reverse Transcriptase Inhibitors / chemical synthesis*
  • Reverse Transcriptase Inhibitors / pharmacology*
  • Spectrophotometry, Infrared
  • Thiazoles / chemical synthesis*
  • Thiazoles / pharmacology*
  • Thymidine / analogs & derivatives*
  • Thymidine / pharmacology
  • Thymine Nucleotides / pharmacology
  • Zidovudine / analogs & derivatives*
  • Zidovudine / pharmacology

Substances

  • Benzimidazoles
  • Benzoxazoles
  • Dideoxynucleotides
  • Indicators and Reagents
  • Pyridines
  • Reverse Transcriptase Inhibitors
  • Thiazoles
  • Thymine Nucleotides
  • 5'-deoxythymidine
  • Zidovudine
  • zidovudine triphosphate
  • HIV Reverse Transcriptase
  • Thymidine