6-chloro-2-oxo-4-[2-(2-methoxyphenyl)ethenyl]-2H-chromene-3-carbonitrile | 1304134-40-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 6-chloro-2-oxo-4-[2-(2-methoxyphenyl)ethenyl]-2H-chromene-3-carbonitrile
• 英文别名: 6-chloro-4-[2-(2-methoxyphenyl)ethenyl]-2-oxochromene-3-carbonitrile
• CAS: 1304134-40-4
• 化学式: C₁₉H₁₂ClNO₃
• 分子量: 337.762
• InChiKey: KWIMHCNQPHIGDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  63.23
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  乙酸-4-氯苯酯 在 哌啶 、 aluminum (III) chloride 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 6-chloro-2-oxo-4-[2-(2-methoxyphenyl)ethenyl]-2H-chromene-3-carbonitrile
  参考文献：
  名称：

  Synthesis and biological evaluation of 4-styrylcoumarin derivatives as inhibitors of TNF-α and IL-6 with anti-tubercular activity

  摘要：

  A series of 4-styrylcoumarin have been synthesized by Knoevenagel condensation between substituted 4-methylcoumarin-3-carbonitrile and different heterocyclic or aromatic aldehydes. 4-Methylcoumarin-3-carbonitrile has been synthesized by the base catalyzed reaction between substituted 2-hydroxyacetophenone and ethyl cyanoacetate. The structures of the newly synthesized compounds were confirmed by H-1 NMR, IR and mass spectral analysis. All the compounds were evaluated for their anti-inflammatory activity (against TNF-alpha and IL-6) and anti-tubercular activity. Compounds 6a, 6h and 6j exhibited promising activity against IL-6 with 72-87% inhibition and compound 6v showed potent activity against TNF-alpha with 73% inhibition at 10 mu M concentration. Whereas compounds 6n, 6o, 6r and 6u showed very good anti-tubercular activity against Mycobacterium tuberculosis H37Rv strain at < 6.25 mu M. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.016