8-methyl-4-(1-methyl-1H-pyrrol-2-yl)-2-oxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile

• 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: 8-methyl-4-(1-methyl-1H-pyrrol-2-yl)-2-oxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile
• 英文别名: 8-methyl-4-(1-methylpyrrol-2-yl)-2-oxo-5,6,7,8-tetrahydro-1H-quinoline-3-carbonitrile
• 化学式: C₁₆H₁₇N₃O
• 分子量: 267.33
• InChiKey: GBYXAMCJROBBDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-甲基-2-吡咯甲醛 、 2-甲基环己酮 、 氰乙酸乙酯 在 ammonium acetate 作用下， 以 neat (no solvent) 为溶剂， 反应 0.17h， 以81%的产率得到8-methyl-4-(1-methyl-1H-pyrrol-2-yl)-2-oxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile
  参考文献：
  名称：

  Microwave-assisted synthesis of certain pyrrolylpyridines, some derived ring systems and their evaluation as anticancer and antioxidant agents

  摘要：

  The synthesis of 18 novel pyrrolylpyridines and some derived bi-, tri- and tetracyclic ring systems using both the conventional heating and MW irradiation techniques is described. Fourteen compounds; 2-9, 10-12, 14, 17 and 18 were evaluated for their antitumor activity according to the National Cancer Institute (NCI), in vitro disease oriented antitumor screening. Distinctive antitumor activity was conjugated with compounds 3 and 7 (R = 3,4-di-OCH3-C6H3). The analogs 3, 6, 7, 9, 10, 11 and 12 which exhibited prominent antitumor activity, were further evaluated for their antioxidant potential using the DPPH radical scavenging assay. The substituted 6-(3,4-dimethoxyphenyl)pyridine-3-carbonitriles 3 and 7 were nearly equipotent to BHT the standard antioxidant utilized in this assay (scavenging activity 31 and 33%, respectively, vs 36%). Accordingly, compounds 3 and 7 can be considered as lead structures for dual antitumor and antioxidant activities. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.01.023