Synthesis and binding properties of new long-chain 4-substituted piperazine derivatives as 5-HT1A and 5-HT7 receptor ligands

Maria N. Modica, Sebastiano Intagliata, Valeria Pittalà, Loredana Salerno, Maria A. Siracusa, Alfredo Cagnotto, Mario Salmona, Giuseppe Romeo

Research output: Contribution to journalArticlepeer-review

Abstract

New long-chain 4-substituted piperazines linked to a thienopyrimidine or a quinazoline system were synthesized and tested for their binding properties on human cloned 5-HT1A and 5-HT7 serotonin receptors. Some structural modifications, concerning tree main portions, that is, terminal fragment, chain length, and aryl substituents, were examined. The 2- and 3-substituted thienopyrimidinone and quinazolinone systems were selected as terminal fragment and a chain length of four or five methylene units was set. Explored aryl substituents were phenyl, phenylmethyl, 3- or 4-chlorophenyl, and 2-ethoxyphenyl. Title compounds showed affinity for 5-HT1A and 5-HT7 receptors. In particular, 2-ethoxyphenyl derivatives 40 and 45 displayed Ki values in the nanomolar range on both receptors, acting as dual ligands.

Original languageEnglish
Pages (from-to)1427-1430
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume25
Issue number7
DOIs
Publication statusPublished - Apr 1 2015

Keywords

  • 5-HT
  • 5-HT
  • Binding properties
  • Ligands
  • Serotonin

ASJC Scopus subject areas

  • Biochemistry
  • Clinical Biochemistry
  • Molecular Biology
  • Molecular Medicine
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science
  • Medicine(all)

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