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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-1 H -imidazol-2-yl)-6,7,8,9-tetrahydro-4 H -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  Ee AChE inhibitor (IC 50  = 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