Identification and synthesis of 2,7-diamino-thiazolo[5,4-d]pyrimidine derivatives as TRPV1 antagonists

Bioorg Med Chem Lett. 2009 Jan 1;19(1):40-6. doi: 10.1016/j.bmcl.2008.11.024. Epub 2008 Nov 13.

Abstract

We have identified and synthesized a series of 2,7-diamino-thiazolo[5,4-d]pyrimidines as TRPV1 antagonists. An exploration of the structure-activity relationships at the 2-, 5-, and 7-positions of the thiazolo[5,4-d]pyrimidine led to the identification of several potent TRPV1 antagonists, including 3, 29, 51, and 57. Compound 3 was orally bioavailable and afforded a significant reversal of carrageenan-induced thermal hyperalgesia with an ED(50)=0.5mg/kg in rats.

MeSH terms

  • Administration, Oral
  • Animals
  • Hyperalgesia / chemically induced
  • Hyperalgesia / drug therapy*
  • Pyrimidines / chemical synthesis*
  • Pyrimidines / pharmacology
  • Rats
  • Structure-Activity Relationship
  • TRPV Cation Channels / antagonists & inhibitors*
  • Thiazoles
  • Treatment Outcome

Substances

  • Pyrimidines
  • TRPV Cation Channels
  • Thiazoles
  • Trpv1 protein, rat