4-[6-(3-Butyl-thioureido)-indol-1-ylmethyl]-3-methoxy-benzoic acid methyl ester | 104446-85-7

• 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: 4-[6-(3-Butyl-thioureido)-indol-1-ylmethyl]-3-methoxy-benzoic acid methyl ester
• CAS: 104446-85-7
• 化学式: C₂₃H₂₇N₃O₃S
• 分子量: 425.552
• InChiKey: WCXFSXOLXCJVGP-UHFFFAOYSA-N

物化性质

• 沸点：
  596.5±60.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.57
• 重原子数：
  30.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  64.52
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-[6-(3-Butyl-thioureido)-indol-1-ylmethyl]-3-methoxy-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 4-[[6-(Butylcarbamothioylamino)indol-1-yl]methyl]-3-methoxybenzoic 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 在 palladium on activated charcoal 氢气 、 溴 、 potassium carbonate 、 溶剂黄146 、 乙酸乙酯 、 乙酰氯 作用下， 以 四氯化碳 、 二氯甲烷 、 丙酮 为溶剂， 反应 184.0h， 生成 4-[6-(3-Butyl-thioureido)-indol-1-ylmethyl]-3-methoxy-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