Ether derivatives of 3-piperidinopropan-1-ol as non-imidazole histamine H3 receptor antagonists

Bioorg Med Chem. 2006 May 15;14(10):3522-9. doi: 10.1016/j.bmc.2006.01.013. Epub 2006 Feb 8.

Abstract

A series of aliphatic and aromatic ether derivatives of 3-piperidinopropan-1-ol has been prepared by four different methods. The ethers obtained were evaluated for their affinities at recombinant human histamine H3 receptor, stably expressed in CHO-K1 or HEK 293 cells. All compounds investigated show from moderate to high in vitro affinities in the nanomolar concentration range. Selected compounds were investigated under in vivo conditions after oral administration to mice. Some proved to be highly potent and orally available histamine H3 receptor antagonists. The most potent antagonists in this series have been in vitro the 4-(1,1-dimethylpropyl)phenyl ether 19 (hH3R K(i) = 8.4 nM) and in vivo the simple ethyl ether 2 (ED50 = 1.0mg/kg).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 1-Propanol / chemistry*
  • 1-Propanol / pharmacology
  • Administration, Oral
  • Animals
  • Cell Line
  • Cells, Cultured
  • Ether / chemistry
  • Ether / pharmacology
  • Ethers / chemistry*
  • Ethers / pharmacology
  • Histamine Antagonists / chemistry*
  • Histamine Antagonists / pharmacology*
  • Humans
  • Imidazoles
  • Mice
  • Molecular Structure
  • Piperidines / chemistry*
  • Piperidines / pharmacology
  • Receptors, Histamine H3 / drug effects*
  • Receptors, Histamine H3 / genetics
  • Recombinant Proteins / genetics

Substances

  • 1-(3-(4-(1,1-dimethylpropyl)phenoxy)propyl)piperidine
  • Ethers
  • Histamine Antagonists
  • Imidazoles
  • Piperidines
  • Receptors, Histamine H3
  • Recombinant Proteins
  • Ether
  • 1-Propanol