(5E/Z)-6-((2S,4R)-1-(tert-butoxycarbonyl)-4-(((4-(trifluoromethyl)phenyl)sulfonyl)amino)pyrrolidin-2-yl)-5-hexenoic acid | 454474-31-8

• 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: (5E/Z)-6-((2S,4R)-1-(tert-butoxycarbonyl)-4-(((4-(trifluoromethyl)phenyl)sulfonyl)amino)pyrrolidin-2-yl)-5-hexenoic acid
• CAS: 454474-31-8
• 化学式: C₂₂H₂₉F₃N₂O₆S
• 分子量: 506.543
• InChiKey: YSPHDLLGDGPVJK-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  113.01
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-氯苯磺酰氯 、 三氟乙酸 、 (5E/Z)-6-((2S,4R)-1-(tert-butoxycarbonyl)-4-(((4-(trifluoromethyl)phenyl)sulfonyl)amino)pyrrolidin-2-yl)-5-hexenoic acid 在 三乙胺 作用下， 以 水 、 二氯甲烷 为溶剂， 反应 3.0h， 以20.5%的产率得到(5Z)-6-((2S,4R)-1-((4-chlorophenyl)sulfonyl)-4-(((4-(trifluoromethyl)phenyl)sulfonyl)amino)pyrrolidin-2-yl)-5-hexenoic acid
  参考文献：
  名称：

  Synthesis and Biological Activity of 1-Phenylsulfonyl-4-Phenylsulfonylaminopyrrolidine Derivatives as Thromboxane A 2 Receptor Antagonists

  摘要：

  The synthesis and biological activity of novel 1-phenylsulfonyl-4- phenylsulfonylaminopyrrolidine analogues are described. All compounds were produced through modification of the substituent formally corresponding to the 1,3-dioxane ring system and the omega-octenol side chain of thromboxane A(2) (TXA(2)), in reference to the structure of Daltroban. Several compounds were found to be potent TXA(2) receptor antagonists. Compound 51a was the most effective inhibitor of 9.11-epoxymethano PGH(2) (U-46619)-induced rat aortic strip contraction (IC50 = 0.48 nM). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00397-2
• 作为产物：
  描述：

  (2S,4R)-BOC-4-苯甲酰氧基脯氨酸甲酯 在 palladium on activated charcoal sodium azide 、 氢气 、 sodium hydride 、 二异丁基氢化铝 、 potassium carbonate 、 三乙胺 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 二甲基亚砜 、 甲苯 为溶剂， -78.0~90.0 ℃ 、303.98 kPa 条件下， 反应 24.0h， 生成 (5E/Z)-6-((2S,4R)-1-(tert-butoxycarbonyl)-4-(((4-(trifluoromethyl)phenyl)sulfonyl)amino)pyrrolidin-2-yl)-5-hexenoic acid
  参考文献：
  名称：

  Synthesis and Biological Activity of 1-Phenylsulfonyl-4-Phenylsulfonylaminopyrrolidine Derivatives as Thromboxane A 2 Receptor Antagonists

  摘要：

  The synthesis and biological activity of novel 1-phenylsulfonyl-4- phenylsulfonylaminopyrrolidine analogues are described. All compounds were produced through modification of the substituent formally corresponding to the 1,3-dioxane ring system and the omega-octenol side chain of thromboxane A(2) (TXA(2)), in reference to the structure of Daltroban. Several compounds were found to be potent TXA(2) receptor antagonists. Compound 51a was the most effective inhibitor of 9.11-epoxymethano PGH(2) (U-46619)-induced rat aortic strip contraction (IC50 = 0.48 nM). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00397-2