Synthesis of new hexahydro- and octahydropyrido[1,2-c]pyrimidine derivatives with an arylpiperazine moiety as ligands for 5-HT1A and 5-HT2A receptors. Part 4

Eur J Med Chem. 2006 Jan;41(1):125-34. doi: 10.1016/j.ejmech.2005.09.003. Epub 2005 Nov 2.

Abstract

New 4-aryl-2H-pyrido[1,2-c]pyrimidine-1,3-dione derivatives of arylpiperazine (6-18) were prepared and evaluated in vitro for their affinity for 5-HT1A, 5-HT2A, and alpha1 receptors. The influence of ortho substitution in the phenyl ring, substitution at position 4 of the pyrido[1,2-c]pyrimidine system, and its unsaturation degree were explored. The tested compounds showed high affinity for the 5-HT1A receptor (Ki = 1.3-79.2 nM) and moderate to low affinity for the 5-HT2A (Ki = 51.7-1405 nM) and alpha1 receptors (Ki = 19.7-382.3 nM). Compounds 8 and 10 showed the highest 5-HT1A receptor affinity (Ki = 1.3 and 2.2 nM, respectively) and were 37- and 35.9-fold, respectively, more selective in relation to alpha1 adrenoreceptors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adrenal Cortex / drug effects
  • Animals
  • Ligands
  • Molecular Structure
  • Piperazines / chemistry*
  • Pyrimidines* / chemical synthesis
  • Pyrimidines* / chemistry
  • Pyrimidines* / metabolism
  • Radioligand Assay
  • Rats
  • Rats, Wistar
  • Receptor, Serotonin, 5-HT1A / metabolism*
  • Receptor, Serotonin, 5-HT2A / metabolism*
  • Structure-Activity Relationship

Substances

  • Ligands
  • Piperazines
  • Pyrimidines
  • Receptor, Serotonin, 5-HT2A
  • octahydropyrido(1,2-c)pyrimidine
  • Receptor, Serotonin, 5-HT1A