Synthesis and evaluation of pyridazinylpiperazines as vanilloid receptor 1 antagonists

Bioorg Med Chem Lett. 2004 Nov 15;14(22):5513-9. doi: 10.1016/j.bmcl.2004.09.010.

Abstract

A structurally biased chemical library of pyridazinylpiperazine analogs was prepared in an effort to improve the pharmaceutical and pharmacological profile of the lead compound N-(4-tertiarybutylphenyl)-4-(3-chloropyridin-2-yl)tetrahydropyrazine-1(2H)-carboxamide (BCTC). The library was evaluated for VR1 antagonist activity in capsaicin-induced (CAP) and pH5.5-induced (pH) FLIPR assays in a human VR1-expressing HEK293 cell line. The most potent VR1 antagonists were found to have IC(50) values in the range of 9-200nM with improved pharmaceutical and pharmacological profiles versus the lead BCTC. These compounds represent possible second-generation BCTC analogs.

MeSH terms

  • Animals
  • Cell Line
  • Drug Evaluation, Preclinical
  • Humans
  • Molecular Structure
  • Piperazines* / chemical synthesis
  • Piperazines* / pharmacology
  • Pyrazines / chemical synthesis
  • Pyrazines / chemistry
  • Pyrazines / pharmacology
  • Pyridazines* / chemical synthesis
  • Pyridazines* / pharmacology
  • Pyridines / chemical synthesis
  • Pyridines / chemistry
  • Pyridines / pharmacology
  • Receptors, Drug / antagonists & inhibitors*
  • TRPV Cation Channels
  • Time Factors

Substances

  • N-(4-tert-butylphenyl)-4-(3-chloropyridin-2-yl)tetrahydropyrazine-1(2H)-carboxamide
  • Piperazines
  • Pyrazines
  • Pyridazines
  • Pyridines
  • Receptors, Drug
  • TRPV Cation Channels
  • TRPV1 receptor