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

descriptionPublicationkeyboard_double_arrow_right Article , Other literature type 24 Mar 2016 Italy, France English Publisher:MDPI AGJournal:Molecules, volume 21, page 400 (eissn: 1420-3049,

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Authors: Boulebd, Houssem; Ismaili, Lhassane; BARTOLINI, MANUELA; Bouraiou, Abdelmalek; ANDRISANO, VINCENZA; Martin, Helene; Bonet, Alexandre; +5 Authors

doi: 10.3390/molecules21040400

pmid: 27023499

pmc: PMC6273229

handle: 10261/149195 , 11585/550121

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

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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).

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Italy, France

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Keywords

hepatotoxicity, cholinesterase inhibitors, 610, antioxidant activity, Organic chemistry, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, Article, Antioxidants, QD241-441, Alzheimer Disease, Humans, Alzheimer's disease; Antioxidant activity; Cholinesterase inhibitors; Hepatotoxicity; ORAC; Tacrine analogues; Organic Chemistry, Oxygen Radical Absorbance Capacity, [CHIM.ORGA]Chemical Sciences/Organic chemistry, tacrine analogues, Imidazoles, Hep G2 Cells, Alzheimer′s disease, Liver, Tacrine, ORAC, Cholinesterase Inhibitors

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