Synthesis, biological assessment and molecular modeling of new dihydroquinoline-3-carboxamides and dihydroquinoline-3-carbohydrazide derivatives as cholinesterase inhibitors, and Ca channel antagonists

Isabelle Tomassoli, Lhassane Ismaili, Marc Pudlo, Cristóbal De Los Ríos, Elena Soriano, Inés Colmena, Luis Gandía, Luis Rivas, Abdelouahid Samadi, José Marco-Contelles, Bernard Refouvelet

Research output: Contribution to journalArticlepeer-review

46 Citations (Scopus)

Abstract

The synthesis, biological evaluation, and molecular modeling of new 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxamides(4), 4-hydroxy-2-oxo-1,2- dihydroquinoline-3-carbohydrazide (6), and some hexahydropyrimido[5,4-c] quinoline-2,5-diones (9) produced earlier by our laboratory, as AChE/BuChE inhibitors, is described. From these analyses compound 4c resulted equipotent regarding the inhibition of cholinesterases'; inhibitors 6k, 9a, 9b were selective for AChE, whereas product 4d proved selective for BuChE. Docking analysis has been carry out in order to identify the binding mode in the active site, and to explain the observed selectivities. Only compound 9a has been shown to decrease K+-induced calcium signals in bovine chromaffin cells.

Original languageEnglish
Pages (from-to)1-10
Number of pages10
JournalEuropean Journal of Medicinal Chemistry
Volume46
Issue number1
DOIs
Publication statusPublished - Jan 2011
Externally publishedYes

Keywords

  • AChE
  • Alzheimer's disease
  • BuChE
  • Ca channel antagonism
  • Dihydroquinoline-3- carbohydrazides
  • Dihydroquinoline-3-carboxamides
  • Molecular modeling
  • hexahydropyrimido[5,4-c]quinoline-2,5-diones

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery
  • Organic Chemistry

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