Synthesis of quinazolinone derivatives containing an acyl hydrazone skeleton as potent anti-urease agents enzyme kinetic studies and anti-oxidant properties

Abstract

This paper covers the synthesis, in vitro urease inhibition, enzyme kinetic parameters, and anti-oxidant studies of a novel series of quinazolinone derivatives containing an acyl hydrazone skeleton. Compounds 3a, 3b, 5a, and 5b, having IC50 values ranging from 1.86 ± 0.07 to 6.38 ± 0.11 µg mL−1, show greater inhibitory activity than the standard inhibitor, thiourea. Among the products, (2-[2-(3-methoxybenzyl)-4-oxoquinazolin-3(4 H)-yl]acetohydrazide) proves to be the most potent, exhibiting enzyme inhibition activity with an IC50 value of 1.86 ± 0.07 µg mL−1. Kinetic studies involving the Lineweaver–Burk plots reveal that the inhibition mechanism of the most active compounds (3a, 3b, 5a, and 5b) on urease activity are found to be in competitive mode. Also, the anti-oxidant activity and radical-scavenging properties of the synthesized compounds are evaluated using cupric reducing anti-oxidant activity, ferric reducing anti-oxidant capacity, 2,2′-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid), and 2,2-diphenyl-1-picrylhydrazyl assays. Compounds 3a, b and 5a, b have good anti-oxidant properties and radical-scavenging activity at various final concentrations.

New derivatives of quinazolinone as an object in the search for substances that exhibit a multi-target effect

“…Охарактеризована способность производных хиназолинона, содержащих ацилгидразоновый фрагмент (рис. 4), проявлять антиуреазную активность [18]. Изучена анти- Использование квантово-химических методов компьютерного моделирования при изучении антимикробной активности новых производных хиназолин-4(3Н)-она позволило авторам спрогнозировать механизм взаимодействия вещества VMA-13-05 (см.…”