Preparation of substituted N-phenyl-4-aryl-2-pyrimidinamines as mediator release inhibitors

J Med Chem. 1993 Sep 17;36(19):2716-25. doi: 10.1021/jm00071a002.

Abstract

The role of immunologically released mediators, such as histamine, leukotrienes, and platelet-activating factor, is well-established for asthma and other allergic disorders. Developing therapeutic agents which would block mediator release from mast cells and other relevant cell types would provide a rational approach to asthma therapy. Using human basophil as a screen, a series of 4-aryl-2-(phenylamino)pyrimidines was found which inhibited mediator release. These compounds were prepared by condensing acetyl heterocycles with dimethylformamide dimethyl acetal to form enaminones which are cyclized with aryl guanidines to give pyrimidines. After examining a large number of analogs, N-[3-(1H-imidazol-1-yl)phenyl]-4-(2-pyridinyl)-2- pyrimidinamine (1-27) was chosen for toxicological evaluation.

MeSH terms

  • Animals
  • Basophils / drug effects
  • Basophils / metabolism
  • Female
  • Histamine Antagonists / chemical synthesis*
  • Humans
  • Imidazoles / chemical synthesis*
  • Imidazoles / chemistry
  • Imidazoles / pharmacology
  • Lethal Dose 50
  • Macaca mulatta
  • Male
  • Mice
  • Passive Cutaneous Anaphylaxis / drug effects
  • Pyrimidines / chemical synthesis*
  • Pyrimidines / chemistry
  • Pyrimidines / pharmacology
  • Rats
  • Rats, Sprague-Dawley
  • Structure-Activity Relationship

Substances

  • Histamine Antagonists
  • Imidazoles
  • Pyrimidines
  • N-(3-(1H-imidazol-1-yl)phenyl)-4-(2-pyridinyl)-2-pyrimidinamine