A new class of potent non-imidazole H(3) antagonists: 2-aminoethylbenzofurans

Bioorg Med Chem Lett. 2004 Feb 9;14(3):689-93. doi: 10.1016/j.bmcl.2003.11.032.

Abstract

2-aminoethylbenzofurans constitute a new class of H(3) antagonists that are more rotationally constrained than most previously reported H(3) antagonists. They retain high potency at human and rat receptors, with efficient CNS penetration observed in 35. The SAR of the basic amine moiety was compared in three different series of analogues. The greatest potency was found in analogues bearing a 2-methylpyrrolidine, a 2,5-dimethylpyrrolidine, or a 2,6-dimethylpiperidine.

Publication types

  • Comparative Study

MeSH terms

  • Amines / chemistry
  • Animals
  • Benzofurans / chemical synthesis*
  • Benzofurans / pharmacology*
  • Central Nervous System / drug effects
  • Histamine Antagonists / chemical synthesis*
  • Histamine Antagonists / pharmacology*
  • Humans
  • Imidazoles / chemistry
  • Molecular Structure
  • Piperidines / chemistry
  • Pyrroles / chemistry
  • Pyrrolidines / chemistry
  • Rats
  • Receptors, Histamine H3 / chemistry
  • Receptors, Histamine H3 / drug effects*
  • Structure-Activity Relationship

Substances

  • Amines
  • Benzofurans
  • Histamine Antagonists
  • Imidazoles
  • Piperidines
  • Pyrroles
  • Pyrrolidines
  • Receptors, Histamine H3
  • N-methylpyrrolidine
  • imidazole
  • 2,5-dimethylpyrrole