Histamine analogues, XXXV: 2-substituted histamine derivatives containing classical moieties of H2-antagonists--a novel class of H1-agonists

Arch Pharm (Weinheim). 1993 Mar;326(3):143-51. doi: 10.1002/ardp.19933260306.

Abstract

A new type of H1-agonists resulted from the combination of the essential histamine structure with parts of H2-antagonists. 2,4-Disubstituted imidazole derivatives were synthesized by reaction of imidic acid methyl esters with 1,3-dihydroxypropanone, 1,4-dihydroxybutanone or 2-oxo-4-phthalimido-1-butylacetate in liquid NH3. The imidazole intermediates were converted into histamine analogues by simple deprotection, Gabriel synthesis followed by deprotection, or by side-chain elongation via the nitriles and final hydrogenation. The new compounds were screened for H1-activity on the isolated guinea-pig ileum and for H2-antagonistic activity on the isolated guinea-pig right atrium. The substances are comparably weak H1-agonists and moderate H2-blockers.

MeSH terms

  • Animals
  • Guinea Pigs
  • Heart Atria / drug effects
  • Histamine / analogs & derivatives*
  • Histamine / chemical synthesis
  • Histamine / pharmacology
  • Histamine Agonists / chemical synthesis*
  • Histamine Agonists / pharmacology
  • Histamine H2 Antagonists / chemical synthesis*
  • Histamine H2 Antagonists / pharmacology
  • In Vitro Techniques
  • Muscle, Smooth / drug effects
  • Structure-Activity Relationship

Substances

  • Histamine Agonists
  • Histamine H2 Antagonists
  • Histamine