4-(6-丁酰氨基-吲哚-1-基甲基)-3-甲氧基-苯甲酸 | 104447-03-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(6-丁酰氨基-吲哚-1-基甲基)-3-甲氧基-苯甲酸
• 英文名称: 4-[[6-(Butanoylamino)indol-1-yl]methyl]-3-methoxybenzoic acid
• CAS: 104447-03-2
• 化学式: C₂₁H₂₂N₂O₄
• 分子量: 366.417
• InChiKey: QHQUPSJAGROVCD-UHFFFAOYSA-N

物化性质

• 熔点：
  225-228 °C
• 沸点：
  657.1±55.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  80.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  methyl 4-<(6-aminoindol-1-yl)methyl>-3-methoxybenzoate 在 lithium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 30.75h， 生成 4-(6-丁酰氨基-吲哚-1-基甲基)-3-甲氧基-苯甲酸
  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

文献信息

• Evolution of a series of peptidoleukotriene antagonists: synthesis and structure-activity relationships of 1,6-disubstituted indoles and indazoles
  作者：Frederick J. Brown、Ying K. Yee、Laura A. Cronk、Kevin C. Hebbel、Robert D. Krell、David W. Snyder

  DOI：10.1021/jm00168a036

  日期：1990.6

  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.