(E)-3-(6-Methoxy-1-methyl-3-pentyl-1H-indol-2-yl)-acryloyl chloride | 121458-70-6

• 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-(6-Methoxy-1-methyl-3-pentyl-1H-indol-2-yl)-acryloyl chloride
• CAS: 121458-70-6
• 化学式: C₁₈H₂₂ClNO₂
• 分子量: 319.831
• InChiKey: UARCGDNQUWFJMN-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  31.23
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R)-α-ethyl-3-pyridinebutanamine 、 (E)-3-(6-Methoxy-1-methyl-3-pentyl-1H-indol-2-yl)-acryloyl chloride 以 甲苯 为溶剂， 反应 1.5h， 生成 -(3-butyl-6-methoxy-1-methyl-2-indolyl)-N-<1-ethyl-4-(3-pyridinyl)butyl>-2-propenamide
  参考文献：
  名称：

  Propenyl carboxamide derivatives as antagonists of platelet-activating factor

  摘要：

  A series of N-[4-(3-pyridinyl)butyl] 3-substituted propenyl carboxamide derivatives bearing an unsaturated bicyclic moiety in the 3-position was prepared and evaluated for PAF (platelet activating factor) antagonist activity. These compounds represent conformationally constrained direct analogues of the corresponding potent 5-aryl-pentadienecarboxamides (5). Most of the new compounds were active in a PAF-binding assay employing whole, washed dog platelets as the receptor source and inhibited PAF-induced bronchoconstriction in guinea pigs after intravenous administration. However, oral activity in the PAF-induced bronchoconstriction model was highly sensitive to the nature and substitution of the bicyclic ring system. The most interesting compounds included [R-(E)]-(1-butyl-6-methoxy-2-naphthyl)-N-[1-methyl-4-(3- pyridinyl)butyl]-2-propenamide (4b), [R-(E)]-(3-butyl-6-methoxy-2- benzo[b]thiophene-yl)-N-[1-methyl-4-(3-pyridinyl)butyl]-2-propenamide (4k), and [R-(E)]-(3-butyl-6-methoxy-1-methyl-2-indoly)-N-[1-ethyl-4- (3-pyridinyl)butyl]-2-propenamide (4l) which inhibited PAF-induced broncho-constriction in guinea pigs with IC50s of 3.0-5.4 mg/kg, when the animals were challenged 2 h after drug treatment. They were also highly effective 6 h after a 50 mg/kg oral dose. This study supports the notion that the key remote aromatic ring present in the 5-arylpentadienecarboxamides (5) is preferentially coplanar with the diene system for good PAF antagonist activity.

  DOI：

  10.1021/jm00172a029
• 作为产物：
  描述：

  6-methoxy-1-methyl-3-pentyl-2-indolecarboxaldehyde 在 sodium hydroxide 、 草酰氯 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 41.33h， 生成 (E)-3-(6-Methoxy-1-methyl-3-pentyl-1H-indol-2-yl)-acryloyl chloride
  参考文献：
  名称：

  Propenyl carboxamide derivatives as antagonists of platelet-activating factor

  摘要：

  A series of N-[4-(3-pyridinyl)butyl] 3-substituted propenyl carboxamide derivatives bearing an unsaturated bicyclic moiety in the 3-position was prepared and evaluated for PAF (platelet activating factor) antagonist activity. These compounds represent conformationally constrained direct analogues of the corresponding potent 5-aryl-pentadienecarboxamides (5). Most of the new compounds were active in a PAF-binding assay employing whole, washed dog platelets as the receptor source and inhibited PAF-induced bronchoconstriction in guinea pigs after intravenous administration. However, oral activity in the PAF-induced bronchoconstriction model was highly sensitive to the nature and substitution of the bicyclic ring system. The most interesting compounds included [R-(E)]-(1-butyl-6-methoxy-2-naphthyl)-N-[1-methyl-4-(3- pyridinyl)butyl]-2-propenamide (4b), [R-(E)]-(3-butyl-6-methoxy-2- benzo[b]thiophene-yl)-N-[1-methyl-4-(3-pyridinyl)butyl]-2-propenamide (4k), and [R-(E)]-(3-butyl-6-methoxy-1-methyl-2-indoly)-N-[1-ethyl-4- (3-pyridinyl)butyl]-2-propenamide (4l) which inhibited PAF-induced broncho-constriction in guinea pigs with IC50s of 3.0-5.4 mg/kg, when the animals were challenged 2 h after drug treatment. They were also highly effective 6 h after a 50 mg/kg oral dose. This study supports the notion that the key remote aromatic ring present in the 5-arylpentadienecarboxamides (5) is preferentially coplanar with the diene system for good PAF antagonist activity.

  DOI：

  10.1021/jm00172a029