Abstract

A series of novel 3-(1-acetyl-5-substitutedphenyl-1H-pyrazol-3-yl)-4-hydroxy-1-methylquinolin-2(1H)-ones (Va–Vf) and 3-(1-acetyl-5-substitutedphenyl-1H-pyrazol-3-yl)-4-hydroxy-1-phenylquinolin-2(1H)-ones (Vg–Vl) were designed and synthesized by the condensation of hydrazine hydrate with (E)-3-(3-(substituted phenyl)acryloyl)-4-hydroxy-1-methyllquinolin-2(1H)-one (IVa–IVf) and (E)-3-(3-(substituted phenyl)acryloyl)-4-hydroxy-1-phenylquinolin-2(1H)-one (IVg–IVl) and these intermediates are prepared from 3-acetyl-4-hydroxy-1-methylquinolin-2(1H)-one (Ia) and 3-acetyl-4-hydroxy-1-phenylquinolin-2(1H)-one (IIa) with diversely functionalized aldehydes (IIIa–IIIf). This synthetic approach provides a new and efficient tool for constructing novel heterocycles on newly synthesized substituted α,β-unsaturated carbonyl compounds. The structures of all the synthesized products were confirmed with their elemental analysis, ¹H NMR, ¹³C NMR, IR, and MS analysis. Further, the newly synthesized compounds were screened for in vitro antibacterial activity against G+ bacteria (S. aureus and B. subtili), G– bacteria (P. aeruginosa and C. albicans), antifungal activity against (C. albicans and A. niger) by using agar well diffusion method. Ciprofloxacin was used as a standard reference drug for antibacterial and Fluconazole drug was used for antifungal activity. The study reveals that the compounds (Ve), (Vf), (Vi), (Vk), and (Vl) showed potential activity against G+ bacteria, and compounds (Vc), (Ve), (Vi), (Vk), and (Vl) showed significant activity against G– bacteria. Compounds (Va), (Vc), (Ve), (Vf), (Vh), (Vi), (Vk), and (Vl) exhibited excellent potential against the antifungal activity.

中文翻译：

---

新型 3-(1-乙酰基-5-取代的苯基-4, 5-二氢-1H-吡唑-3-基)-4-羟基-1-甲基/苯基喹啉-的合成、表征和生物测定的通用方法2(1H)-一衍生物

摘要

一系列新型3-(1-乙酰基-5-取代苯基-1H-吡唑-3-基)-4-羟基-1-甲基喹啉-2(1H ) -酮( Va–Vf )和3-(1 -乙酰基-5-取代苯基-1 H -吡唑-3-基)-4-羟基-1-苯基喹啉-2(1 H )-酮( Vg–VI ) 通过水合肼与( E )的缩合设计并合成)-3-(3-(取代的苯基)丙烯酰基)-4-羟基-1-甲基喹啉-2(1H ) -酮( IVa–IVf )和( E )-3-(3-(取代的苯基)丙烯酰基) -4-羟基-1-苯基喹啉-2(1 H )-酮 ( IVg–IVl），这些中间体由 3-乙酰基-4-羟基-1-甲基喹啉-2(1 H )-酮 ( Ia ) 和 3-乙酰基-4-羟基-1-苯基喹啉-2(1 H )-酮 ( IIa ) 与多种官能化的醛 ( IIIa–IIIf )。这种合成方法为在新合成的取代的α,β-不饱和羰基化合物上构建新型杂环提供了一种新的有效工具。所有合成产物的结构均通过元素分析、¹ H NMR、¹³ C NMR、IR和MS分析得到证实。此外，还筛选了新合成的化合物对 G+ 细菌（金黄色葡萄球菌）的体外抗菌活性。和枯草芽孢杆菌），G-细菌（铜绿假单胞菌和白色念珠菌） ，通过使用琼脂井扩散法对（白色念珠菌和黑曲霉）的抗真菌活性。环丙沙星用作抗菌标准参考药物，氟康唑药物用作抗真菌活性。研究表明，化合物 ( Ve )、( Vf )、( Vi )、( Vk ) 和 ( VI ) 对 G+ 细菌表现出潜在活性，化合物 ( Vc )、( Ve )、( Vi )、( Vk)和( VI )显示出显着的抗G-细菌活性。化合物( Va )、( Vc )、( Ve )、( Vf )、( Vh )、( Vi )、( Vk )和( VI )表现出优异的抗真菌活性潜力。