Synthesis, biological assessment, and molecular modeling of racemic 7-aryl-9,10,11,12-tetrahydro-7H-benzo[7,8]chromeno[2,3-b]quinolin-8-amines as potential drugs for the treatment of Alzheimer's disease

► The synthesis, pharmacology and molecular modeling of tacrine analogs 21-30 are described. ► Tacrine 25 [IC50 (hAChE) = 0.33 ± 0.04 μM] is a mixed type inhibitor (Ki = 81 nM). ► Tacrine 25 shows good antioxidant profile (ORAC experiment: 1.47 ± 0.10 Trolox equiv). ► Inhibitors 26-28 and 30 are permeable, neuroprotective and less toxic than tacrine. ► These tacrine analogs are attractive multipotent therapeutic molecules for AD.