(E)-3-(1-苄基-6-甲氧基-7-甲氧基甲氧基-1H-吲哚-4-基)-2-甲基丙烯酸 | 1027270-94-5

• 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
• 中文名称: (E)-3-(1-苄基-6-甲氧基-7-甲氧基甲氧基-1H-吲哚-4-基)-2-甲基丙烯酸
• 英文名称: (E)-3-[1-benzyl-6-methoxy-7-(methoxymethoxy)indol-4-yl]-2-methylprop-2-enoic acid
• CAS: 1027270-94-5
• 化学式: C₂₂H₂₃NO₅
• 分子量: 381.428
• InChiKey: NASIAKWVQCNJLA-RVDMUPIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  69.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-3-(1-苄基-6-甲氧基-7-甲氧基甲氧基-1H-吲哚-4-基)-2-甲基丙烯酸 在 盐酸 作用下， 以 丙酮 为溶剂， 生成 (E)-3-(1-benzyl-7-hydroxy-6-methoxyindole-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
• 作为产物：
  描述：

  4-羟基-5-甲氧基-2-甲基苯甲醛 在 palladium on activated charcoal 四氢吡咯 、 manganese(IV) oxide 、 氢氧化钾 、 sodium chlorite 、 sodium dihydrogenphosphate 、 氢气 、 硝酸 、 sodium hydride 、 二异丁基氢化铝 、 potassium carbonate 、 溶剂黄146 、 N,N-二异丙基乙胺 、 锌 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， -78.0~85.0 ℃ 、101.33 kPa 条件下， 反应 33.25h， 生成 (E)-3-(1-苄基-6-甲氧基-7-甲氧基甲氧基-1H-吲哚-4-基)-2-甲基丙烯酸
  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

文献信息

• 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
  作者：M Tanaka、M Okita、H Akamatsu、K Chiba、H Obaishi、N Nagakura、H Sakurai、I Yamatsu

  DOI：10.1016/0223-5234(96)89134-3

  日期：1996.1

  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)).