Hit-to-lead optimization of a series of carboxamides of ethyl 2-amino-4-phenylthiazole-5-carboxylates as novel adenosine A2A receptor antagonists

Bioorg Med Chem Lett. 2010 Sep 1;20(17):5241-4. doi: 10.1016/j.bmcl.2010.06.138. Epub 2010 Jul 24.

Abstract

Herein we describe the discovery of a series of novel adenosine A(2A) receptor antagonists. A successful hit-to-lead optimization of an HTS hit led to replacement of a metabolically labile ester moiety with a heteroaromatic group. A compound from the series, (cyclopropanecarboxylic acid [5-(5-methyl-[1,2,4]oxadiazol-3-yl)-4-phenyl-thiazol-2-yl]-amide, compound 13), was shown to be effective in reversing haloperidol-induced hypolocomotion, a model of motor dysfunction in Parkinson's Disease.

MeSH terms

  • Amides / chemistry
  • Amides / pharmacology*
  • Carboxylic Acids / chemistry
  • Carboxylic Acids / pharmacology*
  • Purinergic P1 Receptor Antagonists / chemistry
  • Purinergic P1 Receptor Antagonists / pharmacology*
  • Receptor, Adenosine A2A / drug effects*
  • Structure-Activity Relationship

Substances

  • Amides
  • Carboxylic Acids
  • Purinergic P1 Receptor Antagonists
  • Receptor, Adenosine A2A