Synthesis of N-pyrimidinyl-2-phenoxyacetamides as adenosine A2A receptor antagonists

Bioorg Med Chem Lett. 2008 Mar 15;18(6):1778-83. doi: 10.1016/j.bmcl.2008.02.032. Epub 2008 Feb 16.

Abstract

A series of N-pyrimidinyl-2-phenoxyacetamide adenosine A(2A) antagonists is described. SAR studies led to compound 14 with excellent potency (K(i) = 0.4 nM), selectivity (A(1)/A(2A) > 100), and efficacy (MED 10 mg/kg p.o.) in the rat haloperidol-induced catalepsy model for Parkinson's disease.

MeSH terms

  • Adenosine A2 Receptor Antagonists*
  • Administration, Oral
  • Animals
  • Antiparkinson Agents / chemical synthesis*
  • Antiparkinson Agents / pharmacology
  • Catalepsy / chemically induced
  • Catalepsy / prevention & control*
  • Cytochrome P-450 CYP2D6 / metabolism
  • Cytochrome P-450 CYP2D6 Inhibitors
  • Cytochrome P-450 CYP3A
  • Cytochrome P-450 Enzyme Inhibitors
  • Cytochrome P-450 Enzyme System / metabolism
  • Electrophysiology
  • Ether-A-Go-Go Potassium Channels / antagonists & inhibitors
  • Haloperidol / toxicity
  • Humans
  • Molecular Structure
  • Parkinson Disease / physiopathology*
  • Phenoxyacetates / chemical synthesis*
  • Phenoxyacetates / chemistry
  • Phenoxyacetates / pharmacology
  • Pyrimidines / chemical synthesis*
  • Pyrimidines / chemistry
  • Pyrimidines / pharmacology
  • Rats
  • Structure-Activity Relationship

Substances

  • Adenosine A2 Receptor Antagonists
  • Antiparkinson Agents
  • Cytochrome P-450 CYP2D6 Inhibitors
  • Cytochrome P-450 Enzyme Inhibitors
  • Ether-A-Go-Go Potassium Channels
  • KCNH1 protein, human
  • Phenoxyacetates
  • Pyrimidines
  • Cytochrome P-450 Enzyme System
  • Cyp3a2 protein, rat
  • Cytochrome P-450 CYP2D6
  • Cytochrome P-450 CYP3A
  • Haloperidol