Substituted 7-amino-5-thio-thiazolo[4,5-d]pyrimidines as potent and selective antagonists of the fractalkine receptor (CX3CR1)

J Med Chem. 2013 Apr 25;56(8):3177-90. doi: 10.1021/jm3012273. Epub 2013 Apr 4.

Abstract

We have developed two parallel series, A and B, of CX3CR1 antagonists for the treatment of multiple sclerosis. By modifying the substituents on the 7-amino-5-thio-thiazolo[4,5-d]pyrimidine core structure, we were able to achieve compounds with high selectivity for CX3CR1 over the closely related CXCR2 receptor. The structure-activity relationships showed that a leucinol moiety attached to the core-structure in the 7-position together with α-methyl branched benzyl derivatives in the 5-position displayed promising affinity, and selectivity as well as physicochemical properties, as exemplified by compounds 18a and 24h. We show the preparation of the first potent and selective orally available CX3CR1 antagonists.

MeSH terms

  • Amino Alcohols / chemical synthesis
  • Amino Alcohols / pharmacokinetics
  • Amino Alcohols / pharmacology
  • Animals
  • CX3C Chemokine Receptor 1
  • Caco-2 Cells
  • Humans
  • Multiple Sclerosis / drug therapy*
  • Pyrimidines / chemical synthesis
  • Pyrimidines / chemistry
  • Pyrimidines / pharmacokinetics
  • Pyrimidines / pharmacology*
  • Rats
  • Receptors, Chemokine / antagonists & inhibitors*
  • Structure-Activity Relationship
  • Thiazoles / chemical synthesis
  • Thiazoles / chemistry
  • Thiazoles / pharmacokinetics
  • Thiazoles / pharmacology*

Substances

  • AZD8797
  • Amino Alcohols
  • CX3C Chemokine Receptor 1
  • CX3CR1 protein, human
  • Pyrimidines
  • Receptors, Chemokine
  • Thiazoles