Synthesis, crystal structure and cholinesterase enzymes inhibitory activities of new pyridine alkaloid derivative

• Main Authors: Ghalib, Gaza Murad, Hashim, Rokiah, Mehdi, Sayed Hasan, Da Silva, M. Fátima C. Guedes, Sulaiman, Othman, How, Fiona Ni Foong, Kawamura, Fumio, Jawad, Ali, Algamal, Yousif, Chan, Kit-Lam, Murugaiyah, Vikneswaran
• Format: Article
• Language: English
• Published: India 2015
• Subjects: QD Chemistry
• Online Access: http://irep.iium.edu.my/46444/1/Asian_journal_of_chemistry_%284092-4096%29.pdf; http://irep.iium.edu.my/46444/; http://www.asianjournalofchemistry.co.in/User/ViewFreeArticle.aspx?ArticleID=27_11_35

A new pyridine alkaloid derivative named as 2-(6-benzyl-4-oxo-5-phenyl-1,4-dihydro pyridine-3-yl)-benzoic acid ethylester (3) has been prepared by the reaction of ninhydrin with 1,3-diphenylacetonep-tosylhydrazone and the structure has been established with the help of spectral analysis and X-ray analysis. The title compound demonstrated potent inhibitory activity against butyrylcholinesterase (BChE; IC50 = 4.91 µM) comparable to physostigmine (IC50 = 4.72 x 10-1 µM). However it showed moderate inhibitory activity against acetylcholinesterase (AChE; IC50 = 82.00 µM)). It was BChE selective over AChE, in contrast to physostigmine, which was more AChE selective. Being a potent and selective BChE inhibitor, it may serve as a new class of drug for prevention of the progression of neurodegeneration as well for symptomatic treatment of Alzheimer patient.