Histamine H1 receptor ligands: part II. Synthesis and in vitro pharmacology of 2-[2-(phenylamino)thiazol-4-yl]ethanamine and 2-(2-benzhydrylthiazol-4-yl)ethanamine derivatives

Farmaco. 2000 Sep-Oct;55(9-10):569-74. doi: 10.1016/s0014-827x(00)00087-2.

Abstract

New 2-[2-(phenylamino)thiazol-4-yl]ethanamine and 2-(2-benzhydrylthiazol-4-yl)ethanamine derivatives were prepared and tested in vitro as H1 receptor antagonists. The compounds with 2-phenylamino substitution with meta-halide substituents at the phenyl ring, showed weak H1-antagonistic activity (pA2: 4.62-5.04) and this activity was completely lost in the case of meta-methyl substituent (pA2 < 4). When the phenylamino group was replaced by benzhydryl groups of classic antihistamines, the resulting compounds exhibited slightly improved H1-antagonistic activity (at the meta-position pA2: 6.38-6.15; at the para-position pA2: 6.04-5.87).

MeSH terms

  • Animals
  • Ethylamines / chemical synthesis
  • Ethylamines / chemistry
  • Ethylamines / pharmacology*
  • Guinea Pigs
  • Histamine Antagonists / chemical synthesis
  • Histamine Antagonists / chemistry
  • Histamine Antagonists / pharmacology*
  • Ligands
  • Male
  • Molecular Structure
  • Receptors, Histamine H1 / metabolism*
  • Thiazoles / chemical synthesis
  • Thiazoles / chemistry
  • Thiazoles / pharmacology*

Substances

  • Ethylamines
  • Histamine Antagonists
  • Ligands
  • Receptors, Histamine H1
  • Thiazoles