In this study, a series of multifunctional hybrids (6a-6l) against Alzheimer's disease were designed and obtained by conjugating the pharmacophores of deoxyvasicinone and indole. These analogs of deoxyvasicinone-indole were evaluated as inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE), and as inhibitors of amyloid aggregation (Aβ<sub>1-42</sub>) for treatment of Alzheimer's disease (AD). Subsequently, AChE induced Aβ aggregation inhibition test was also performed for selected compounds. Biological activity results demonstrated that compound 6b was the most potent and balanced dual ChEs inhibitor with IC<sub>50</sub> values 0.12 µM and 0.15 µM for eeAChE and eqBuChE, respectively. Kinetic analysis and docking study indicated that compound 6b was a mixed-type inhibitor for both AChE and BuChE. Compound 6b also found to be the best inhibitors of self-induced Aβ<sub>1-42</sub> aggregation with IC<sub>50</sub> values of 1.21 µM. Compound 6b also afforded excellent inhibition of AChE-induced Aβ<sub>1-42</sub> aggregation by 81.1%. Overall, these results indicate that 6b may be considered as lead compound for the development of highly effective anti-AD drugs.