Experimental and Theoretical Approaches in the Study of Phenanthroline-Tetrahydroquinolines for Alzheimer's Disease

Yorley Duarte, Margarita Gutierrez, Rocío Álvarez, Jans H. Alzate-Morales, Jorge Soto-Delgado

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

The imino-Diels-Alder reaction is one of the most common strategies in organic chemistry and is an important tool for providing a broad spectrum of biologically active heterocyclic systems. A combined theoretical and experimental study of the imino-Diels-Alder reaction is described. The new phenanthroline-tetrahydroquinolines were evaluated as cholinesterase inhibitors. Their cytotoxicity in human neuroblastoma SH-SY5Y cells was also evaluated. The theoretical results suggest that compounds formation in stages can be explained by endo cycloadducts under the established reaction conditions, thereby confirming experimental results obtained for percentage yield. These results allowed us to establish that pyridine substituent remarkably influences activation energy and reaction yield, as well as in acetylcholinesterase (AChE) activity. Among these derivatives, compounds with 4-pyridyl and 4-nitrophenyl showed favorable AChE activity and proved to be non-cytotoxic.

Original languageEnglish
Pages (from-to)627-636
Number of pages10
JournalChemistryOpen
Volume8
Issue number5
DOIs
Publication statusPublished - 1 May 2019

Keywords

  • acetylcholinesterase
  • Alzheimer's disease imino-Diels-Alder
  • density functional theory
  • tetrahydroquinolines

ASJC Scopus subject areas

  • Chemistry(all)

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