3-((2-phenylhydrazono)methyl)quinolin-2(1H)-one | 344447-41-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-((2-phenylhydrazono)methyl)quinolin-2(1H)-one
• 英文别名: 3-[(phenylhydrazinylidene)methyl]-1H-quinolin-2-one
• CAS: 344447-41-2
• 化学式: C₁₆H₁₃N₃O
• 分子量: 263.299
• InChiKey: PGQRPWNRDCTQOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  53.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-乙酰苯胺 在 水 、 溶剂黄146 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 生成 3-((2-phenylhydrazono)methyl)quinolin-2(1H)-one
  参考文献：
  名称：

  Synthesis and Antitumor Activities of Some 2-Oxo-quinoline-3-Schiff Base Derivatives

  摘要：

  一系列2-氧代喹啉-3-席夫碱衍生物（4a1-4n2）被设计并合成为新型抗肿瘤药物。在体外对四种癌细胞系（MGC80-3、BEL-7404、A549和NCI-H460）进行了抗肿瘤活性评估。化合物4a1、4a2、4c2、4d1、4d2和4l2在NCI-H460上的抑制活性优于商业抗肿瘤药物5-氟尿嘧啶（5-氟尿嘧啶，IC50 = 44 ± 0.54 μM），其IC50值分别为35.52 ± 0.86、16.22 ± 0.71、11.62 ± 0.52、5.16 ± 0.37、7.62 ± 0.46和7.66 ± 0.65 μM。

  DOI：

  10.14233/ajchem.2014.17186

文献信息

• Synthesis and biological activity on IBD virus of diverse heterocyclic systems derived from 2-cyano-<i>N</i>'-((2-oxo-1,2-dihydroquinolin-3-yl)methylene)acetohydrazide
  作者：Mohamed M. Kaddah、Alaa R. I. Morsy、Abdelgawad A. Fahmi、Mustafa M. Kamel、Mounir M. Elsafty、Sameh A. Rizk、Sayed K. Ramadan

  DOI：10.1080/00397911.2021.1970776

  日期：2021.11.17

  2-dihydroquinolin-3-yl)methylene)ethanohydrazide (3) was synthesized in 87% yield via condensation of 3-formyl-2-oxoquinoline (1) with 2-cyanoethanohydrazide (2). The titled compound was then treated with some electrophilic reagents to construct some novel quinoline-based heterocyclic systems, for example, pyrazole, thiazoline, pyridine, pyrimidine, chromene, and thiophene derivatives. The behavior of the

  摘要 A 2氰基Ñ “ - （（2-氧代-1,2-二氢喹啉-3-基）亚甲基）ethanohydrazide（3）中通过的缩合产率87％合成3-甲酰基-2-氧代喹啉（1）与2-氰基乙醇酰肼 ( 2 )。然后用一些亲电子试剂处理标题化合物以构建一些新的基于喹啉的杂环系统，例如吡唑、噻唑啉、吡啶、嘧啶、色烯和噻吩衍生物。检查了标题化合物对肼和苯肼的行为。七种物质的体外筛选对无特定病原体 (SPF) 鸡胚胎中传染性法氏囊病病毒 (IBDV) 的抗病毒活性以及评估这些物质在 SPF 小鸡中的免疫增强特性。抗病毒结果表明，与参考药物利巴韦林相比，化合物5a和17表现出最强的效力。因此，它们被认为是IBVD疫苗疫苗生产中很有前景的抗病毒添加剂，以增加免疫刺激剂。
• Synthesis and antioxidant activities of 2-oxo-quinoline-3-carbaldehyde Schiff-base derivatives
  作者：Ye Zhang、Yilin Fang、Hong Liang、Hengshan Wang、Kun Hu、Xianxian Liu、Xianghui Yi、Yan Peng

  DOI：10.1016/j.bmcl.2012.11.006

  日期：2013.1

  A series of 2-oxo-quinoline-3-carbaldehyde Schiff-base derivatives 4a(1)-4n(2) were designed and synthesized based on the 2-oxo-quinoline structure core as novel antioxidants. In vitro antioxidant activities of these compounds were evaluated and compared with commercial antioxidants ascorbic acid, BHT and BHA, employing DPPH center dot assay, ABTS(+center dot) assay, O-2(-center dot) assay and OH center dot assay. The results showed that IC50 of most compounds were lower than standard value 10 mg/mL, indicating good antioxidant activities of these compounds. In addition, in vitro antioxidant activities screening revealed that 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activities of compounds 4b(2), 4e(1), 4e(2) and 4g(2), 2,2'-azinobis-(3-ethylbenzthiazoline-6-sulphonate) cation (ABTS(+)) radical scavenging activities of compounds 4a(1), 4e(1), 4e(2), 4f(1), 4f(2), 4g(1), 4g(2), 4h(1), 4h(2), 4k(1), 4k(2), 4n(1) and 4n(2), superoxide anion radical scavenging activities of 4b(1), 4e(1), 4f(2), 4j(1), 4k(1), 4k(2), 4m(1), 4m(2), and 4n(2), and hydroxyl radical scavenging activity of almost all the compounds except 4f(1), 4f(2), 4j(2), 4l(1) and 4l(2) were better than that of the commercial antioxidant butylated hydroxytoluene (BHT). (C) 2012 Elsevier Ltd. All rights reserved.