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Molecules 2016, 21(4), 400; doi:10.3390/molecules21040400

Imidazopyranotacrines as Non-Hepatotoxic, Selective Acetylcholinesterase Inhibitors, and Antioxidant Agents for Alzheimer's Disease Therapy

1
Equipe de Synthèse de Molécules à Objectif Thérapeutique, Laboratoire des Produits Naturels d′Origine Végétale et de Synthèse Organique (PHYSYNOR), Université des frères Mentouri, Campus de Chaabat-Ersas, Constantine 25000, Algeria
2
Laboratoire de Chimie Organique et Thérapeutique, Neurosciences Intégratives et Cliniques EA 481, UFR SMP, Univ. Franche-Comté, Univ. Bourgogne Franche-Comté, 19, rue Ambroise Paré, F-Besançon 25000, France
3
Department of Pharmacy and Biotechnology, University of Bologna, Via Belmeloro 6, Bologna 40126, Italy
4
Department for Life Quality Studies, University of Bologna, Corso d′Augusto, 237, Rimini 47921, Italy
5
Laboratoire de Toxicologie Cellulaire, EA 4267, Univ. Bourgogne Franche-Comté, 19, rue Ambroise Paré, Besançon Cedex 25030, France
6
Departamento de Química Orgánica y Química Inorgánica, Facultad de Biología, Ciencias Ambientales y Química, Universidad de Alcalá, Ctra. Barcelona, Km. 33.5, Alcalá de Henares 28817, Spain
7
Laboratory of Medicinal Chemistry (IQOG, CSIC), C/Juan de la Cierva 3, Madrid 28006, Spain
*
Authors to whom correspondence should be addressed.
Academic Editors: Michael Decker and Diego Muñoz-Torrero
Received: 27 January 2016 / Revised: 11 March 2016 / Accepted: 15 March 2016 / Published: 24 March 2016
(This article belongs to the Special Issue Molecules against Alzheimer)
View Full-Text   |   Download PDF [1053 KB, uploaded 24 March 2016]   |  

Abstract

Herein we describe the synthesis and in vitro biological evaluation of thirteen new, racemic, diversely functionalized imidazo pyranotacrines as non-hepatotoxic, multipotent tacrine analogues. Among these compounds, 1-(5-amino-2-methyl-4-(1-methyl-1H-imidazol-2-yl)-6,7,8,9-tetrahydro-4H-pyrano[2,3-b]quinolin-3-yl)ethan-1-one (4) is non-hepatotoxic (cell viability assay on HepG2 cells), a selective but moderately potent EeAChE inhibitor (IC50 = 38.7 ± 1.7 μM), and a very potent antioxidant agent on the basis of the ORAC test (2.31 ± 0.29 μmol·Trolox/μmol compound). View Full-Text
Keywords: tacrine analogues; hepatotoxicity; cholinesterase inhibitors; antioxidant activity; ORAC; Alzheimer′s disease tacrine analogues; hepatotoxicity; cholinesterase inhibitors; antioxidant activity; ORAC; Alzheimer′s disease
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Boulebd, H.; Ismaili, L.; Bartolini, M.; Bouraiou, A.; Andrisano, V.; Martin, H.; Bonet, A.; Moraleda, I.; Iriepa, I.; Chioua, M.; Belfaitah, A.; Marco-Contelles, J. Imidazopyranotacrines as Non-Hepatotoxic, Selective Acetylcholinesterase Inhibitors, and Antioxidant Agents for Alzheimer's Disease Therapy. Molecules 2016, 21, 400.

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