N-[(6-methyl-2-oxo-1H-quinolin-3-yl)methylideneamino]pyridine-4-carboxamide | 850745-55-0

• 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: N-[(6-methyl-2-oxo-1H-quinolin-3-yl)methylideneamino]pyridine-4-carboxamide
• CAS: 850745-55-0
• 化学式: C₁₇H₁₄N₄O₂
• 分子量: 306.324
• InChiKey: GZHRDGZUTVUDHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  83.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-甲基乙酰苯胺 在 水 、 溶剂黄146 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 生成 N-[(6-methyl-2-oxo-1H-quinolin-3-yl)methylideneamino]pyridine-4-carboxamide
  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 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.
• Kumar, M.R. Pradeep; Joshi; Dixit, Indian Journal of Heterocyclic Chemistry, 2014, vol. 23, # 4, p. 353 - 358
  作者：Kumar, M.R. Pradeep、Joshi、Dixit、Kulkarni

  DOI：——

  日期：——
• Synthesis and Antitumor Activities of Some 2-Oxo-quinoline-3-Schiff Base Derivatives
  作者：Yilin Fang、Xianghui Yi、Wen Qin、Ye Zhang、Yongzhi Liao

  DOI：10.14233/ajchem.2014.17186

  日期：——

  A series of 2-oxo-quinoline-3-Schiff-base derivatives (4a1-4n2) have been designed and synthesized as new antitumor agents. in vitro Antitumor activities were evaluated against four cancer cell lines including MGC80-3, BEL-7404, A549 and NCI-H460. Compounds 4a1, 4a2, 4c2, 4d1, 4d2 and 4l2 exhibited better inhibition activities than commercial antitumor drug 5-fluorouracil (5-fluorouracil, IC50 = 44 ± 0.54 μM) on NCI-H460, with IC50 of 35.52 ± 0.86, 16.22 ± 0.71, 11.62 ± 0.52, 5.16 ± 0.37, 7.62 ± 0.46 and 7.66 ± 0.65 μM, respectively.

  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。