4-(4-{(E)-3-[1-(1-Propyl-butyl)-1H-indol-5-yl]-but-2-enoylamino}-phenoxy)-butyric acid ethyl ester | 1026029-80-0

• 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
• 英文名称: 4-(4-{(E)-3-[1-(1-Propyl-butyl)-1H-indol-5-yl]-but-2-enoylamino}-phenoxy)-butyric acid ethyl ester
• 英文别名: ethyl 4-[4-[[(E)-3-(1-heptan-4-ylindol-5-yl)but-2-enoyl]amino]phenoxy]butanoate
• CAS: 1026029-80-0
• 化学式: C₃₁H₄₀N₂O₄
• 分子量: 504.67
• InChiKey: HHHQXTXSAMBAAI-XTQSDGFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  37
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  69.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-{(E)-3-[1-(1-Propyl-butyl)-1H-indol-5-yl]-but-2-enoylamino}-phenoxy)-butyric acid ethyl ester 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 生成 4-(4-{(E)-3-[1-(1-Propyl-butyl)-1H-indol-5-yl]-but-2-enoylamino}-phenoxy)-butyric acid
  参考文献：
  名称：

  (E)-4-{2-[[3-(Indol-5-yl)-1-oxo-2-butenyl]amino]phenoxy}butyric Acid Derivatives: A New Class of Steroid 5.alpha.-Reductase Inhibitors in the Rat Prostate. 1

  摘要：

  A series of (E)-4-{2-[[3-(indol-5-yl)-1-oxo-2-butenyl]amino]phenoxy}butyric acid derivatives was prepared, and the derivatives were demonstrated to be potent inhibitors of steroid 5 alpha-reductase in the rat prostate. The structure-activity relationships were as follows. An alpha-branched alkyI or benzyl substituent of proper size at position I of the indole is crucial for optimal enzyme inhibitory activity. N-Methylation of the amide NH resulted in complete loss of activity. Thus, coplanarity of the benzene ring and amide moiety is essential for such activity. Among the compounds prepared, (E)-4-(2-[[3-[1-[bis(4-fluorophenyl)methyl]indol-5-yl]-1-oxo-2-butenyl]amino]phenoxy)butyric acid (57, KF18678) was one of the most potent compounds (rat prostate 5 alpha-reductase IC50 = 3.3 nM).

  DOI：

  10.1021/jm00015a011
• 作为产物：
  描述：

  (E)-3-[1-(1-Propyl-butyl)-1H-indol-5-yl]-but-2-enoic acid ethyl ester 在 lithium hydroxide 、 三正丁胺 、 2-chloromethylpyridinium iodide 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 4-(4-{(E)-3-[1-(1-Propyl-butyl)-1H-indol-5-yl]-but-2-enoylamino}-phenoxy)-butyric acid ethyl ester
  参考文献：
  名称：

  (E)-4-{2-[[3-(Indol-5-yl)-1-oxo-2-butenyl]amino]phenoxy}butyric Acid Derivatives: A New Class of Steroid 5.alpha.-Reductase Inhibitors in the Rat Prostate. 1

  摘要：

  A series of (E)-4-{2-[[3-(indol-5-yl)-1-oxo-2-butenyl]amino]phenoxy}butyric acid derivatives was prepared, and the derivatives were demonstrated to be potent inhibitors of steroid 5 alpha-reductase in the rat prostate. The structure-activity relationships were as follows. An alpha-branched alkyI or benzyl substituent of proper size at position I of the indole is crucial for optimal enzyme inhibitory activity. N-Methylation of the amide NH resulted in complete loss of activity. Thus, coplanarity of the benzene ring and amide moiety is essential for such activity. Among the compounds prepared, (E)-4-(2-[[3-[1-[bis(4-fluorophenyl)methyl]indol-5-yl]-1-oxo-2-butenyl]amino]phenoxy)butyric acid (57, KF18678) was one of the most potent compounds (rat prostate 5 alpha-reductase IC50 = 3.3 nM).

  DOI：

  10.1021/jm00015a011

文献信息

• (E)-4-{2-[[3-(Indol-5-yl)-1-oxo-2-butenyl]amino]phenoxy}butyric Acid Derivatives: A New Class of Steroid 5.alpha.-Reductase Inhibitors in the Rat Prostate. 1
  作者：Toshiaki Kumazawa、Hitoshi Takami、Nobuyuki Kishibayashi、Akio Ishii、Yoshitomo Nagahara、Noriaki Hirayama、Hiroyuki Obase

  DOI：10.1021/jm00015a011

  日期：1995.7

  A series of (E)-4-2-[[3-(indol-5-yl)-1-oxo-2-butenyl]amino]phenoxy}butyric acid derivatives was prepared, and the derivatives were demonstrated to be potent inhibitors of steroid 5 alpha-reductase in the rat prostate. The structure-activity relationships were as follows. An alpha-branched alkyI or benzyl substituent of proper size at position I of the indole is crucial for optimal enzyme inhibitory activity. N-Methylation of the amide NH resulted in complete loss of activity. Thus, coplanarity of the benzene ring and amide moiety is essential for such activity. Among the compounds prepared, (E)-4-(2-[[3-[1-[bis(4-fluorophenyl)methyl]indol-5-yl]-1-oxo-2-butenyl]amino]phenoxy)butyric acid (57, KF18678) was one of the most potent compounds (rat prostate 5 alpha-reductase IC50 = 3.3 nM).