Multi-substituted 8-aminoimidazo[1,2-a]pyrazines by Groebke-Blackburn-Bienaymé reaction and their Hsp90 inhibitory activity

Org Biomol Chem. 2015 Feb 7;13(5):1531-5. doi: 10.1039/c4ob01865f.

Abstract

Using a 2,3-diamino pyrazine substrate and yttrium triflate catalyst, various 2-alkyl and aryl substituted 3,8-diaminoimidazo[1,2-a]pyrazines were efficiently prepared through Groebke-Blackburn-Bienaymé MCR. In particular, a novel 2-piperonyl 3,8-diaminoimidazo[1,2-a]pyrazine structure was prepared exclusively with this new method and was found to have moderate Hsp90 inhibitory activity. A crystalline complex with N-terminus ATP domain of Hsp90 and one of the new Hsp90 inhibitors was also obtained to elucidate the origin of activity of 2-piperonyl 3,8-diaminoimidazo[1,2-a]pyrazines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Drug Design
  • HSP90 Heat-Shock Proteins / antagonists & inhibitors*
  • HSP90 Heat-Shock Proteins / chemistry
  • Models, Molecular
  • Protein Conformation
  • Pyrazines / chemistry*
  • Pyrazines / pharmacology*

Substances

  • HSP90 Heat-Shock Proteins
  • Pyrazines