Solution phase parallel synthesis of substituted 3-phenylsulfonyl-[1,2,3]triazolo[1,5-a]quinazolines: selective serotonin 5-HT(6) receptor antagonists

J Comb Chem. 2010 Jul 12;12(4):445-52. doi: 10.1021/cc1000049.

Abstract

Here we present the solution phase parallel synthesis of a combinatorial library consisting of 776 new substituted 3-phenylsulfonyl-[1,2,3]triazolo[1,5-a]quinazolines and a study of the relation of their structure with a 5-HT(6) receptor antagonistic activity in a functional cell (HEK 293) analysis and radioligand competitive binding. We have found highly active and selective 5-HT(6)R antagonists. The most active 5-HT(6)R antagonists have IC(50) <100 nM in a functional assay, and K(i) <10 nM in a binding assay, which is 100 times higher than the activity with respect to other serotonin receptors.

MeSH terms

  • Cell Line
  • Combinatorial Chemistry Techniques
  • Humans
  • Molecular Structure
  • Quinazolines / chemical synthesis*
  • Quinazolines / chemistry
  • Quinazolines / pharmacology*
  • Receptors, Serotonin / chemistry*
  • Small Molecule Libraries
  • Solutions
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Quinazolines
  • Receptors, Serotonin
  • Small Molecule Libraries
  • Solutions
  • serotonin 6 receptor