Synthesis of novel diarylpyrimidine analogues of TMC278 and their antiviral activity against HIV-1 wild-type and mutant strains

Eur J Med Chem. 2007 May;42(5):567-79. doi: 10.1016/j.ejmech.2006.11.014. Epub 2006 Dec 15.

Abstract

Novel diarylpyrimidines (DAPY), which represent next generation of non-nucleoside reverse transcriptase inhibitors (NNRTIs), were synthesized and their activities against human immunodeficiency virus type I (HIV-1) assessed. Modulations at positions 2 and 6 of the left phenyl ring generated interesting derivatives of TMC278 displaying high potency against wild-type and mutant viruses compared to nevirapine and efavirenz. The pharmacokinetic profile of the best newly synthesized DAPY was evaluated and compared with TMC278 now in phase II clinical trials.

MeSH terms

  • Animals
  • Chromatography, High Pressure Liquid
  • Dogs
  • Female
  • HIV-1 / drug effects*
  • Magnetic Resonance Spectroscopy
  • Male
  • Mass Spectrometry
  • Nitriles / chemical synthesis*
  • Nitriles / pharmacology*
  • Pyrimidines / chemical synthesis
  • Pyrimidines / chemistry*
  • Pyrimidines / pharmacology
  • Rats
  • Rats, Wistar
  • Reverse Transcriptase Inhibitors / chemical synthesis*
  • Reverse Transcriptase Inhibitors / pharmacology*
  • Rilpivirine
  • Spectrophotometry, Ultraviolet

Substances

  • Nitriles
  • Pyrimidines
  • Reverse Transcriptase Inhibitors
  • Rilpivirine