(Z)-7-((1R,2R,3R,5S)-5-hydroxy-2-((3R,E)-4-phenoxy-3-((tetrahydro-2H-pyran-2-yl)oxy)but-1-en-1-yl)-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)-N-(methylsulfonyl)hept-5-enamide | 64282-81-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (Z)-7-((1R,2R,3R,5S)-5-hydroxy-2-((3R,E)-4-phenoxy-3-((tetrahydro-2H-pyran-2-yl)oxy)but-1-en-1-yl)-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)-N-(methylsulfonyl)hept-5-enamide
• CAS: 64282-81-1
• 化学式: C₃₃H₄₉NO₉S
• 分子量: 635.819
• InChiKey: NEIJYKWQDYITCX-FHBBPMGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.63
• 重原子数：
  44.0
• 可旋转键数：
  16.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  129.62
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (Z)-7-((1R,2R,3R,5S)-5-hydroxy-2-((3R,E)-4-phenoxy-3-((tetrahydro-2H-pyran-2-yl)oxy)but-1-en-1-yl)-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)-N-(methylsulfonyl)hept-5-enamide 在 jones reagent 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 反应 14.08h， 生成 硫前列酮
  参考文献：
  名称：

  N-(Methanesulfonyl)-16-phenoxyprostaglandin carboxamides: tissue-selective, uterine stimulants

  摘要：

  In an effort to develop tissue-selective prostaglandin analogues resistant to the metabolic inactivating pathways of the natural materials, hybrid compounds modified both at C-1 with a sulfonimide moiety and in the n-amylcarbinol side chain with substituted phenoxy groups were synthesized and evaluated in a variety of in vitro models. Several of these analogues exhibited potent, tissue-selective, uterine stimulant activity, a finding subsequently confirmed in clinical studies with one member of this series, N-(methanesulfonyl)-16-phenoxy-omega-tetranor-PGE2-carboxamide (CP-34089/ZK-57671, sulprostone).

  DOI：

  10.1021/jm00143a018
• 作为产物：
  描述：

  苯氧乙酸甲酯 在 sodium methylsulfinylcarbanide 、 sodium hydride 、 二异丁基氢化铝 、 三乙基硼氢化锂 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 7.83h， 生成 (Z)-7-((1R,2R,3R,5S)-5-hydroxy-2-((3R,E)-4-phenoxy-3-((tetrahydro-2H-pyran-2-yl)oxy)but-1-en-1-yl)-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)-N-(methylsulfonyl)hept-5-enamide
  参考文献：
  名称：

  N-(Methanesulfonyl)-16-phenoxyprostaglandin carboxamides: tissue-selective, uterine stimulants

  摘要：

  In an effort to develop tissue-selective prostaglandin analogues resistant to the metabolic inactivating pathways of the natural materials, hybrid compounds modified both at C-1 with a sulfonimide moiety and in the n-amylcarbinol side chain with substituted phenoxy groups were synthesized and evaluated in a variety of in vitro models. Several of these analogues exhibited potent, tissue-selective, uterine stimulant activity, a finding subsequently confirmed in clinical studies with one member of this series, N-(methanesulfonyl)-16-phenoxy-omega-tetranor-PGE2-carboxamide (CP-34089/ZK-57671, sulprostone).

  DOI：

  10.1021/jm00143a018