Methyl <1α,2α(Z),3β,4α>-(+/-)-7-<3-<(2-oxo-2-ethyl)thio>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoate | 119785-46-5

• 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: Methyl <1α,2α(Z),3β,4α>-(+/-)-7-<3-<(2-oxo-2-ethyl)thio>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoate
• CAS: 119785-46-5
• 化学式: C₁₆H₂₄O₄S
• 分子量: 312.43
• InChiKey: YYMYPQGAVUWIDP-JMKNJONMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Methyl <1α,2α(Z),3β,4α>-(+/-)-7-<3-<(2-oxo-2-ethyl)thio>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoate 在 氢氧化钾 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 、 xylene 为溶剂， 反应 7.5h， 生成 <1α,2α(Z),3α,4α>-(+/-)-7-<3-(Heptylthio)-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoic acid
  参考文献：
  名称：

  9,11-Epoxy-9-homo-14-thiaprost-5-enoic acid derivatives: potent thromboxane A2 antagonists

  摘要：

  A novel bicyclic prostaglandin analogue, (1S)-[1 alpha,2 alpha(Z),3 alpha,4 alpha]-7-[3-[(hexylthio)methyl]-7- oxabicyclo [2.2.1]hept-2-yl]-5-heptenoic acid ((-)-10), and its cogeners were found to be potent antagonists at the TxA2 receptor. Compound (-)-10 was the only stereoisomer out of eight possible structures that was active. Thioether (-)-10 was 30-40-fold more potent than another TxA2 antagonist, BM 13.177, in inhibiting arachidonic acid (AA) induced aggregation of human platelet-rich plasma. Compound (-)-10 was effective (I50 = 0.5 +/- 0.4 microM) in inhibiting 9,11-azo-PGH2-induced (0.1 microgram/mL) contraction of guinea pig tracheal spirals. The bronchoconstriction in anesthetized guinea pigs induced by AA was also effectively antagonized by (-)-10 (1 mg/kg, iv); however, in this assay (-)-10 exhibited some direct agonist activity. Radioligand binding studies in washed (human) platelets revealed that (-)-10 is one of the most potent ligands for the PGH2/TxA2 receptor yet described (Kd = 1.6 +/- 0.4 nM).

  DOI：

  10.1021/jm00125a009
• 作为产物：
  描述：

  methyl <1β,2α(Z),3α,4β>-7-(3-hydroxy-7-oxabicyclo<2.2.1>hept-2-yl)-5-heptenoate 、 硫代乙酸 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以33%的产率得到Methyl <1α,2α(Z),3β,4α>-(+/-)-7-<3-<(2-oxo-2-ethyl)thio>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoate
  参考文献：
  名称：

  9,11-Epoxy-9-homo-14-thiaprost-5-enoic acid derivatives: potent thromboxane A2 antagonists

  摘要：

  A novel bicyclic prostaglandin analogue, (1S)-[1 alpha,2 alpha(Z),3 alpha,4 alpha]-7-[3-[(hexylthio)methyl]-7- oxabicyclo [2.2.1]hept-2-yl]-5-heptenoic acid ((-)-10), and its cogeners were found to be potent antagonists at the TxA2 receptor. Compound (-)-10 was the only stereoisomer out of eight possible structures that was active. Thioether (-)-10 was 30-40-fold more potent than another TxA2 antagonist, BM 13.177, in inhibiting arachidonic acid (AA) induced aggregation of human platelet-rich plasma. Compound (-)-10 was effective (I50 = 0.5 +/- 0.4 microM) in inhibiting 9,11-azo-PGH2-induced (0.1 microgram/mL) contraction of guinea pig tracheal spirals. The bronchoconstriction in anesthetized guinea pigs induced by AA was also effectively antagonized by (-)-10 (1 mg/kg, iv); however, in this assay (-)-10 exhibited some direct agonist activity. Radioligand binding studies in washed (human) platelets revealed that (-)-10 is one of the most potent ligands for the PGH2/TxA2 receptor yet described (Kd = 1.6 +/- 0.4 nM).

  DOI：

  10.1021/jm00125a009