(E)-3-(7-hydroxy-6-methoxy-3-methyl-2-phenyl-1-propylindole-4-yl)-2-methylpropenoic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (E)-3-(7-hydroxy-6-methoxy-3-methyl-2-phenyl-1-propylindole-4-yl)-2-methylpropenoic acid
• 英文别名: (E)-3-(7-hydroxy-6-methoxy-3-methyl-2-phenyl-1-propylindol-4-yl)-2-methylprop-2-enoic acid
• 化学式: C₂₃H₂₅NO₄
• 分子量: 379.456
• InChiKey: WXEAIRFDCRQLNJ-WYMLVPIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  71.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-溴苯丙酮 在 盐酸 、 氢氧化钾 、 potassium hydrogensulfate 、 正丁基锂 、 双氧水 、 三溴化硼 、 sodium hydride 、 三氯氧磷 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 乙二醇甲醚 、 丙酮 为溶剂， 反应 21.0h， 生成 (E)-3-(7-hydroxy-6-methoxy-3-methyl-2-phenyl-1-propylindole-4-yl)-2-methylpropenoic acid
  参考文献：
  名称：

  Hydroxyindole derivatives as inhibitors of IL-1 generation. II. Synthesis and pharmacological activities of (E)-3-(7-hydroxy-6-methoxyindole-4-yl)-2-methylpropenoic acid derivatives

  摘要：

  A series of (E)-3-(7-hydroxy-6-methoxyindole-4-yl)-2-methylpropenoic acid derivatives was prepared and the inhibitory activities of its members on IL-1 generation were evaluated in an in vitro system using exudate cells from the rat carboxymethyl cellulose (CMC) induced air-pouch model. All the compounds in this new series were found to be inhibitors of IL-1 generation. In particular, the methoxy-substituted 2-phenyl compounds 28d-f were the most potent inhibitors of IL-1 generation (eg, 28d: IC50 = 0.8 mu M). The compounds in this series also inhibited IL-1 alpha and IL-1 beta generations in an in vitro system using human monocytes stimulated with LPS (eg, 28b: IC50 = 1.4 mu M (IL-1 alpha) and 0.9 mu M (IL-1 beta)).

  DOI：

  10.1016/0223-5234(96)89134-3