Design, Synthesis, and Biological Activity of Amide Based on Isoquinolinium Salts

Abstract

A series of novel aminoacetamides based on isoquinolinium salts was designed by molecular hybridization of the aminoacetamide scaffold and isoquinoline motif. The target compounds were synthesized and their biological activities were evaluated. Some of the target molecules showed excellent antifungal activities against Sclerotinia sclerotiorum. Significantly, 2-{2-[(4-methoxyphenyl)amino]-2-oxoethyl}isoquinolin-2-ium chloride displayed the most potent activity against Sclerotinia sclerotiorum with EC₅₀ = 13.59 μg/mL. Additionally, 2-{2-[(4-methoxyphenyl)amino]-2-oxoethyl}isoquinolin-2-ium chloride, 2-[2-oxo-2-(propylamino)ethyl]isoquinolin-2-ium chloride, 2-[2-(butylamino)-2-oxoethyl]isoquinolin-2-ium chloride and 2-[2-oxo-2-(pentylamino)ethyl]isoquinolin-2-ium chloride showed better acetylcholinesterase inhibition than positive control tacrine.