4-(2-thiazolylcarbamoyl)chalcone-2'-carboxylic acid

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 4-(2-thiazolylcarbamoyl)chalcone-2'-carboxylic acid
• 英文别名: 2-[(E)-3-[4-(1,3-thiazol-2-ylcarbamoyl)phenyl]prop-2-enoyl]benzoic acid
• 化学式: C₂₀H₁₄N₂O₄S
• 分子量: 378.408
• InChiKey: IIIMTHLXBXTBGW-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  125
• 氢给体数：
  2
• 氢受体数：
  6

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	4-formyl-N-(2-thiazolyl)benzamide	147729-75-7	C11H8N2O2S	232.263

反应信息

• 作为反应物：
  描述：

  甲醇 、 4-(2-thiazolylcarbamoyl)chalcone-2'-carboxylic acid 在 硫酸 作用下， 反应 16.0h， 以82%的产率得到2-{(E)-3-[4-(Thiazol-2-ylcarbamoyl)-phenyl]-acryloyl}-benzoic acid methyl ester
  参考文献：
  名称：

  2'-Substituted chalcone derivatives as inhibitors of interleukin-1 biosynthesis

  摘要：

  A series of 2'-substituted chalcone derivatives has been found to show potent inhibition of the production of IL-1beta from human peripheral blood monocytes stimulated with lipopolysaccharide (LPS), with IC50 values in the 0.2-5.0-muM range. Some members of the series have also shown inhibition of septic shock induced in mice by injection of LPS, although with low potency. Qualitative structure-activity relationships have shown that the enone is required for activity, which may be mediated by conjugate addition of a biological nucleophile to the chalcone. Electron-poor aromatic rings beta to the ketone give enhanced potency. Although electronic effects in the other ring (directly attached to the ketone) are minimal, this ring must possess an ortho substituent for good activity without cytotoxicity, suggesting a degree of selectivity which would not be expected for simple, nonspecific alkylating agents.

  DOI：

  10.1021/jm00062a016
• 作为产物：
  描述：

  4-甲酰基苯甲酰氯 在 sodium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 13.0h， 生成 4-(2-thiazolylcarbamoyl)chalcone-2'-carboxylic acid
  参考文献：
  名称：

  2'-Substituted chalcone derivatives as inhibitors of interleukin-1 biosynthesis

  摘要：

  A series of 2'-substituted chalcone derivatives has been found to show potent inhibition of the production of IL-1beta from human peripheral blood monocytes stimulated with lipopolysaccharide (LPS), with IC50 values in the 0.2-5.0-muM range. Some members of the series have also shown inhibition of septic shock induced in mice by injection of LPS, although with low potency. Qualitative structure-activity relationships have shown that the enone is required for activity, which may be mediated by conjugate addition of a biological nucleophile to the chalcone. Electron-poor aromatic rings beta to the ketone give enhanced potency. Although electronic effects in the other ring (directly attached to the ketone) are minimal, this ring must possess an ortho substituent for good activity without cytotoxicity, suggesting a degree of selectivity which would not be expected for simple, nonspecific alkylating agents.

  DOI：

  10.1021/jm00062a016