Ultrasound-assisted synthesis of novel chalcone, heterochalcone and bis-chalcone derivatives and the evaluation of their antioxidant properties and as acetylcholinesterase inhibitors

Efraín Polo, N. Ibarra-Arellano, Luis Prent-Peñaloza, Alejandro Morales-Bayuelo, José Henao, Antonio Galdámez, Margarita Gutiérrez

Research output: Contribution to journalArticlepeer-review

22 Citations (Scopus)

Abstract

The chalcone and bis-chalcone derivatives have been synthesized under sonication conditions via Claisen-Schmidt condensation with KOH in ethanol at room temperature (20–89%). The structures were established on the basis of NMR, IR, Single-crystal XRD, and MS. The best compound 3u had inhibitory activity (IC50 = 7.50 µM). The synthesis, the antioxidative properties, chemical reactivity descriptors supported in Density Functional Theory (DFT), acetylcholinesterase (AChE) inhibition and their potential binding modes, and affinity were predicted by molecular docking of a number of morpholine-chalcones and quinoline-chalcone. A series of bis-chalcones are also reported. Molecular docking and an enzyme kinetic study on compound 3u suggested that it simultaneously binds to the catalytic active site (CAS) and peripheral anionic site (PAS) of AChE. Moreover, the pharmacokinetic profile of these compounds was investigated using a computational method.

Original languageEnglish
Article number103034
JournalBioorganic Chemistry
Volume90
DOIs
Publication statusPublished - Sep 2019
Externally publishedYes

Keywords

  • Alzheimer's disease
  • Antioxidant
  • Bis-chalcones
  • Chalcones
  • Molecular modeling

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Drug Discovery
  • Organic Chemistry

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