<1α,2α(Z),3α(E),4α>-7-<3-(3-hydroxy-5-phenyl-1-pentenyl)-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoic acid | 85873-60-5

• 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: <1α,2α(Z),3α(E),4α>-7-<3-(3-hydroxy-5-phenyl-1-pentenyl)-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoic acid
• CAS: 85873-60-5
• 化学式: C₂₄H₃₂O₄
• 分子量: 384.516
• InChiKey: RDLAXLDILGQZHL-ABBYYHALSA-N

物化性质

• 沸点：
  574.9±40.0 °C(Predicted)
• 密度：
  1.157±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  28.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  66.76
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (Z)-7-[(1S,2R,3S,4R)-3-((E)-3-Oxo-5-phenyl-pent-1-enyl)-7-oxa-bicyclo[2.2.1]hept-2-yl]-hept-5-enoic acid methyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 <1α,2α(Z),3α(E),4α>-7-<3-(3-hydroxy-5-phenyl-1-pentenyl)-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoic acid
  参考文献：
  名称：

  9,11-Epoxy-9-homoprosta-5-enoic acid analogs as thromboxane A2 receptor antagonists

  摘要：

  A novel bicyclic prostaglandin analogue, (1S)-[1 alpha, 2 alpha(Z),3 alpha(1E,3S*,4R*),4 alpha]-7-[3-(3-hydroxy-4-phenyl-1-pentenyl)-7- oxabicyclo[2.2.1]hept-2-yl]-5-heptenoic acid (4), was found to be a potent and selective thromboxane A2 (TxA2) receptor antagonist. Alcohol 4 was the only member in a series of allylic alcohols which did not display direct contractile activity in the rat stomach strip model. Alcohol 4 was effective in the inhibition of (a) arachidonic acid induced platelet aggregation of human platelet-rich plasma (I50 = 0.65 +/- 0.1 microM); (b) 11,9-epoxymethano-PGH2 induced contraction of guinea pig trachea (pA2 = 8.0 +/- 0.2) or rat aorta (pA2 = 8.1 +/- 0.2); and (c) arachidonic acid induced bronchoconstriction in the anesthetized guinea pig (1 mg/kg iv). A radioiodinated analogue of 4 bound in a specific and saturable manner to human platelet membranes with a Kd = 2.3 +/- 0.9 nM. Modification of the alpha-chain, in an attempt to minimize in vivo metabolism, resulted in TxA2 receptor antagonists of reduced in vitro potency.

  DOI：

  10.1021/jm00168a032