2α-(6'carboxyhex-2'Z-enyl)-3β-(3''-hydroxyoct-1''E-enyl)-6-oxabicyclo<3.2.1>octane

• 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: 2α-(6'carboxyhex-2'Z-enyl)-3β-(3''-hydroxyoct-1''E-enyl)-6-oxabicyclo<3.2.1>octane
• 英文别名: 2α-(6'carboxyhex-2'Z-enyl)-3β-(3''-hydroxyoct-1''E-enyl)-6-oxabicyclo[3.2.1]octane；(Z)-7-[(1S,2R,3R,5S)-3-[(E,3R)-3-hydroxyoct-1-enyl]-6-oxabicyclo[3.2.1]octan-2-yl]hept-5-enoic acid
• 化学式: C₂₂H₃₆O₄
• 分子量: 364.525
• InChiKey: LIMSUSWAFIDGDS-WLOFLUCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2-氧代庚基)膦酸二甲酯 在 aluminum isopropoxide 、 sodium hydride 作用下， 以 异丙醇 、 甲苯 为溶剂， 反应 8.5h， 生成 2α-(6'carboxyhex-2'Z-enyl)-3β-(3''-hydroxyoct-1''E-enyl)-6-oxabicyclo<3.2.1>octane
  参考文献：
  名称：

  Thromboxane receptor active analogues based on the 6-oxabicyclo[3.2.1]octane ring system

  摘要：

  Prostanoid analogues with a 6-oxabicyclo[3.2.1]octane ring and 3 different types of omega-chain have been synthesized and evaluated for biological activity on thromboxane A2 (TXA2) receptors and prostaglandin I2 (PGI2) receptors. The standard omega-chain analogue 34b is a TXA2 receptor agonist approximately 10-fold less potent than U46619 3, the standard agonist. The O-diphenyl-methyloximino-omega'-chain analogue 32 gives a PGI2-like agonist almost-equal-to 5-fold less active than EP 157, the most active molecule in this class. Conversely, 4-arylsemicarbazone omega-chain analogues 35a and 35b show TXA2 antagonism comparable to that obtained with bicyclo[2.2.2]octane and bicyclo[2.2. 1]heptane systems containing this type of omega-chain (eg EP 092).

  DOI：

  10.1016/0223-5234(93)90092-s

文献信息

• Thromboxane receptor active analogues based on the 6-oxabicyclo[3.2.1]octane ring system
  作者：G Muir、RL Jones、SG Will、T Winwick、V Peesapati、NH Wilson、N Griffiths、WV Nicholson、P Taylor、L Sawyer、AJ Blake

  DOI：10.1016/0223-5234(93)90092-s

  日期：1993.1

  Prostanoid analogues with a 6-oxabicyclo[3.2.1]octane ring and 3 different types of omega-chain have been synthesized and evaluated for biological activity on thromboxane A2 (TXA2) receptors and prostaglandin I2 (PGI2) receptors. The standard omega-chain analogue 34b is a TXA2 receptor agonist approximately 10-fold less potent than U46619 3, the standard agonist. The O-diphenyl-methyloximino-omega'-chain analogue 32 gives a PGI2-like agonist almost-equal-to 5-fold less active than EP 157, the most active molecule in this class. Conversely, 4-arylsemicarbazone omega-chain analogues 35a and 35b show TXA2 antagonism comparable to that obtained with bicyclo[2.2.2]octane and bicyclo[2.2. 1]heptane systems containing this type of omega-chain (eg EP 092).