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-4Hpyrano[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).
Imidazopyranotacrines as Non-Hepatotoxic, Selective Acetylcholinesterase Inhibitors, and Antioxidant Agents for Alzheimer's Disease Therapy / Boulebd, Houssem; Ismaili, Lhassane; Bartolini, Manuela; Bouraiou, Abdelmalek; Andrisano, Vincenza; Martin, Helene; Bonet, Alexandre; Moraleda, Ignacio; Iriepa, Isabel; Chioua, Mourad; Belfaitah, Ali; Marco-Contelles, José. - In: MOLECULES. - ISSN 1420-3049. - ELETTRONICO. - 21:4(2016), pp. 400.1-400.16. [10.3390/molecules21040400]
Imidazopyranotacrines as Non-Hepatotoxic, Selective Acetylcholinesterase Inhibitors, and Antioxidant Agents for Alzheimer's Disease Therapy
BARTOLINI, MANUELA;ANDRISANO, VINCENZA;
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-4Hpyrano[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).| File | Dimensione | Formato | |
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