(E)-3-(1-Ethyl-6-methoxy-7-methoxymethoxy-2,3-dimethyl-1H-indol-4-yl)-2-methyl-acrylic acid ethyl ester | 1026723-92-1

• 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: (E)-3-(1-Ethyl-6-methoxy-7-methoxymethoxy-2,3-dimethyl-1H-indol-4-yl)-2-methyl-acrylic acid ethyl ester
• 英文别名: ethyl (E)-3-[1-ethyl-6-methoxy-7-(methoxymethoxy)-2,3-dimethylindol-4-yl]-2-methylprop-2-enoate
• CAS: 1026723-92-1
• 化学式: C₂₁H₂₉NO₅
• 分子量: 375.465
• InChiKey: JFDFSYWCTIXKOA-JLHYYAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  58.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-3-(1-Ethyl-6-methoxy-7-methoxymethoxy-2,3-dimethyl-1H-indol-4-yl)-2-methyl-acrylic acid ethyl ester 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 生成 (E)-3-(1-Ethyl-6-methoxy-7-methoxymethoxy-2,3-dimethyl-1H-indol-4-yl)-2-methyl-acrylic 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
• 作为产物：
  描述：

  2,3-Dimethyl-7-methoxyindol 在 盐酸 、 potassium hydrogensulfate 、 正丁基锂 、 双氧水 、 tetra-N-butylammonium tribromide 、 三溴化硼 、 sodium hydride 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 丙酮 为溶剂， 反应 10.5h， 生成 (E)-3-(1-Ethyl-6-methoxy-7-methoxymethoxy-2,3-dimethyl-1H-indol-4-yl)-2-methyl-acrylic acid ethyl ester
  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