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

Overview

Journal ChemistryOpen

Specialty Chemistry

Date 2019 May 30

PMID 31139552

Citations 2

Authors

Yorley Duarte

Margarita Gutierrez

Rocio Alvarez

Jans H Alzate-Morales

Jorge Soto-Delgado

Affiliations

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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 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.

Citing Articles

Validation of Acetylcholinesterase Inhibition Machine Learning Models for Multiple Species.

Vignaux P, Lane T, Urbina F, Gerlach J, Puhl A, Snyder S Chem Res Toxicol. 2023; 36(2):188-201.

PMID: 36737043 PMC: 9945174. DOI: 10.1021/acs.chemrestox.2c00283.

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

Duarte Y, Gutierrez M, Alvarez R, Alzate-Morales J, Soto-Delgado J ChemistryOpen. 2019; 8(5):627-636.

PMID: 31139552 PMC: 6528641. DOI: 10.1002/open.201900073.

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