3-(((4-hydroxyphenyl)imino)methyl)quinolin-2(1H)-one | 1416985-91-5

• 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-(((4-hydroxyphenyl)imino)methyl)quinolin-2(1H)-one
• 英文别名: 3-[(4-hydroxyphenyl)iminomethyl]-1H-quinolin-2-one
• CAS: 1416985-91-5
• 化学式: C₁₆H₁₂N₂O₂
• 分子量: 264.283
• InChiKey: FSNUEQLXEGBTGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氯-3-喹啉甲醛 在 水 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 3-(((4-hydroxyphenyl)imino)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, Molecular Docking and Antimicrobial Activities of 3-Formyl-2- (1H)quinolinone Schiff Base Derivatives and 3-(((3-Acetylphenyl)imino)- methyl)quinolin-2-(1H)-one Chalcone Derivatives
  作者：Mansoura Ali、sohier maigali、hanaa tawfik、Fouad Soliman、Maysa Mohramb、Mahmoud dondeti

  DOI：10.21608/ejchem.2020.27574.2580

  日期：2020.5.10

  Some of Schiff base derivatives were separated by condensing 3-formyl-2-quinolinone with various primary amine derivatives in ethanol, in which water is expelled. Moreover, substituted acryloylphenyliminomethylquinolinone chalcone derivatives were prepared by the process of condensation reaction of aldehyde derivatives with 3-acetylphenylquinolinone in dilute solution of ethanolic sodium hydroxide

  一些席夫碱衍生物是通过将3-甲酰基-2-喹啉酮与各种伯胺衍生物在乙醇中缩合而分离的，其中的水被排出。此外，通过将醛衍生物与3-乙酰基苯基喹啉酮在乙醇氢氧化钠的稀溶液中通过克莱森-施密特缩合方法缩合反应的方法，制备了取代的丙烯酰基苯基亚氨基甲基喹啉酮查尔酮衍生物。还研究了喹啉酮查耳酮与丙二腈，苯肼，脲和硫脲的环化反应。这些化合物的结构已根据光谱数据阐明。还评估了新产品的抗微生物活性。
• 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.