Discovery of substituted benzyl tetrazoles as histamine H3 receptor antagonists

Bioorg Med Chem Lett. 2010 Sep 1;20(17):5165-9. doi: 10.1016/j.bmcl.2010.07.009.

Abstract

A series of potent and subtype selective H3 receptor antagonists containing a novel tetrazole core and diamine motif is reported. A one-pot multi-component Ugi reaction was utilised to rapidly develop the structure-activity relationships (SAR) of these compounds. Optimisation for liver microsome stability (t(1/2)>60 min), minimal CYP inhibition (IC(50)>50 microM) and high cell permeability (Caco-2 P(app) >20x10(-6) cm/s) identified several compounds with drug-like properties.

MeSH terms

  • Caco-2 Cells
  • Cell Membrane Permeability
  • Drug Discovery
  • Half-Life
  • Histamine H3 Antagonists / chemistry
  • Histamine H3 Antagonists / pharmacokinetics
  • Histamine H3 Antagonists / pharmacology*
  • Humans
  • Microsomes, Liver / drug effects
  • Microsomes, Liver / metabolism
  • Structure-Activity Relationship
  • Tetrazoles / chemistry
  • Tetrazoles / pharmacokinetics
  • Tetrazoles / pharmacology*

Substances

  • Histamine H3 Antagonists
  • Tetrazoles