3-(2,4-dimethoxy-phenyl)-1-indol-3-yl-propenone | 27664-02-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-(2,4-dimethoxy-phenyl)-1-indol-3-yl-propenone
• 英文别名: 3-(2,4-dimethoxyphenyl)-1-(1H-indol-3-yl)prop-2-en-1-one
• CAS: 27664-02-4
• 化学式: C₁₉H₁₇NO₃
• 分子量: 307.349
• InChiKey: NVIUIVOCQGFEEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.08
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  51.32
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  3-乙酰吲哚 、 2,4-二甲氧基苯甲醛 在 氯化亚砜 作用下， 以 甲醇 为溶剂， 反应 0.2h， 生成 3-(2,4-dimethoxy-phenyl)-1-indol-3-yl-propenone
  参考文献：
  名称：

  Synthesis, antitubercular activity, and molecular modeling studies of analogues of isoliquiritigenin and liquiritigenin, bioactive components from Glycyrrhiza glabra

  摘要：

  Isoliquiritigenin (ISL, 1) and liquiritigenin (LTG, 2) were isolated from the rhizomes of Glycyrrhiza glabra. In an attempt to develop potent and selective antituberculosis agents, a series of ISL analogues were synthesized mainly via acid- and base-catalyzed Claisen-Schmidt condensation reaction for their antitubercular activity. Compared to ISL (MIC = 25 mu g/mL), analogues 5, 8, and 10 showed similar antitubercular activity, but, interestingly, 6, 7, and 15 exhibited twofold higher activity (MIC = 12.5 mu g/mL) over ISL, against Mycobacterium tuberculosis. Among the LTG derivatives, LTG 4'-acetate and LTG-oxime were found to be as active (MIC = 25 mu g/mL) as LTG. It is the first report on antimycobacterial activity of these ISL- and LTG-based derivatives. Molecular docking and in silico ADME studies revealed that compounds 6, 7, and 15 are potent inhibitors of M. tuberculosis H(37)Rv alanine dehydrogenase and showed compliance with standard parameters of drug likeness.

  DOI：

  10.1007/s00044-015-1401-1