1,2-Dihydro-6-methyl-2-oxo-3-quinolinecarboxaldehyde 3-oxime | 878669-97-7

• 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: 1,2-Dihydro-6-methyl-2-oxo-3-quinolinecarboxaldehyde 3-oxime
• 英文别名: 3-(hydroxyiminomethyl)-6-methyl-1H-quinolin-2-one
• CAS: 878669-97-7
• 化学式: C₁₁H₁₀N₂O₂
• 分子量: 202.213
• InChiKey: ZSQJBEZVYMIXGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.64
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  65.45
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  4-甲基乙酰苯胺 在 水 、 羟胺 、 溶剂黄146 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 生成 1,2-Dihydro-6-methyl-2-oxo-3-quinolinecarboxaldehyde 3-oxime
  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

• Novel quinoline derivatives carrying nitrones/oximes nitric oxide donors: Design, synthesis, antiproliferative and caspase-3 activation activities
  作者：Mahmoud S. Abdelbaset、Mohamed Abdel-Aziz、Gamal El-Din A. Abuo-Rahma、Mostafa H. Abdelrahman、Mohamed Ramadan、Bahaa G. M. Youssif

  DOI：10.1002/ardp.201800270

  日期：——

  Novel quinoline derivatives carrying nitrones and oxime as nitric oxide donors were prepared and characterized using different spectroscopic techniques. Nitrones can release nitric oxide in larger amounts compared to corresponding oximes. Antiproliferative screening results showed that the 2‐benzylthioquinoline nitrones 6e and 6f and the 2‐methylthio analogues 6g and 6h exhibited promising antiproliferative

  使用不同的光谱技术制备并表征了携带硝酮和肟作为一氧化氮供体的新型喹啉衍生物。与相应的肟相比，硝酮可以释放更大量的一氧化氮。抗增殖筛选结果表明，2-苄硫基喹啉硝酮 6e 和 6f 以及 2-甲硫基类似物 6g 和 6h 表现出有希望的抗增殖活性，尤其是对白血病和结肠癌细胞系。与阿霉素相比，化合物 6c、6e 和 6f 作为抗癌剂表现出更高的效力，IC50 范围为 0.45 至 0.91 μM。在用测试化合物处理的细胞中观察到 caspase-3 蛋白水平的显着过表达。与其他阶段相比，化合物 6e 在 G2/M 期表现出更多的前 G1 细胞凋亡和细胞周期停滞。
• 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.