3-Methoxy-4-[6-(2-phenyl-propionylamino)-indol-1-ylmethyl]-benzoic acid methyl ester | 104435-84-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-Methoxy-4-[6-(2-phenyl-propionylamino)-indol-1-ylmethyl]-benzoic acid methyl ester
• CAS: 104435-84-9
• 化学式: C₂₇H₂₆N₂O₄
• 分子量: 442.514
• InChiKey: YETLZSGZGLMTJO-UHFFFAOYSA-N

物化性质

• 沸点：
  688.7±55.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.23
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  69.56
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-Methoxy-4-[6-(2-phenyl-propionylamino)-indol-1-ylmethyl]-benzoic acid methyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 30.0h， 生成 3-Methoxy-4-[[6-(2-phenylpropanoylamino)indol-1-yl]methyl]benzoic acid
  参考文献：
  名称：

  Evolution of a series of peptidoleukotriene antagonists: synthesis and structure-activity relationships of 1,6-disubstituted indoles and indazoles

  摘要：

  A perception of structural similarities between two independent series of leukotriene antagonists (one emanating from FPL 55712 and one based upon the leukotrienes themselves) led to the discovery of a novel class of indole and indazole derived antagonists of peptidoleukotrienes. A systematic exploration of C-6 substituted 4-(indol-1-ylmethyl)-3-methoxybenzoic acids identified cyclopentylacetamide and cyclopentylurethane as preferred substituents. The corresponding indazoles were equipotent. These compounds are selective leukotriene antagonists with pKB values of 7.5-7.8 vs LTE4 on guinea pig trachea.

  DOI：

  10.1021/jm00168a036
• 作为产物：
  描述：

  3-甲氧基-4-甲基苯甲酸甲酯 在 palladium on activated charcoal 氢气 、 溴 、 potassium carbonate 、 溶剂黄146 、 乙酸乙酯 、 N,N'-羰基二咪唑 作用下， 以 四氯化碳 、 二氯甲烷 、 丙酮 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 100.5h， 生成 3-Methoxy-4-[6-(2-phenyl-propionylamino)-indol-1-ylmethyl]-benzoic acid methyl ester
  参考文献：
  名称：

  Evolution of a series of peptidoleukotriene antagonists: synthesis and structure-activity relationships of 1,6-disubstituted indoles and indazoles

  摘要：

  A perception of structural similarities between two independent series of leukotriene antagonists (one emanating from FPL 55712 and one based upon the leukotrienes themselves) led to the discovery of a novel class of indole and indazole derived antagonists of peptidoleukotrienes. A systematic exploration of C-6 substituted 4-(indol-1-ylmethyl)-3-methoxybenzoic acids identified cyclopentylacetamide and cyclopentylurethane as preferred substituents. The corresponding indazoles were equipotent. These compounds are selective leukotriene antagonists with pKB values of 7.5-7.8 vs LTE4 on guinea pig trachea.

  DOI：

  10.1021/jm00168a036