Synthesis of piperine analogues as AChE and BChE inhibitors for the treatment of Alzheimer's disease

Phytochemistry Letters
2023.0

Abstract

Piperine 1, an alkaloid isolated from the black pepper plant (Piper nigrum L.), has been reported to possess various biological activities. Here, this compound was converted to piperine amide derivatives (3a-3z) through condensation with several piperazine derivatives and secondary amines. All the synthesized compounds have been tested in vitro to evaluate their activities in the field of Alzheimer's disease therapy, in particular their antioxidant and inhibition of AChE and BChE activities. Most of the synthesized compounds showed good antioxidant behavior and also potent inhibition of AChE and BChE activities. Among them, para-pyridyl piper-azine 3c was the most potent AChE inhibitor with an IC50 value of 51.7 mu M, while piperine amide derivatives 3 v, 3x and 3z had better BChE inhibitory activities than galantamine, with IC50 values ranging from 4.0 to 15.4 mu M. The most active compounds exhibited competitive and noncompetitive inhibitions against AChE and BChE ac-tivities, respectively. The docking studies also showed good binding energies towards the target enzymes. These results may facilitate the design and development of novel anti-Alzheimer's drugs based on natural piperine.

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