<1α,2β(Z),3β,4α>-(+/-)-7-<3-<(Hexylthio)methyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoic acid | 119785-29-4

• 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,2β(Z),3β,4α>-(+/-)-7-<3-<(Hexylthio)methyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoic acid
• 英文别名: (Z)-7-[(1S,2S,3R,4R)-3-(hexylsulfanylmethyl)-7-oxabicyclo[2.2.1]heptan-2-yl]hept-5-enoic acid
• CAS: 119785-29-4
• 化学式: C₂₀H₃₄O₃S
• 分子量: 354.554
• InChiKey: YHSIOGBAMKKEDO-NNNSSLJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  24
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-己硫醇 在 lithium hydroxide 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 <1α,2β(Z),3β,4α>-(+/-)-7-<3-<(Hexylthio)methyl>-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

文献信息

• US4654364A
  申请人：——

  公开号：US4654364A

  公开（公告）日：1987-03-31
• US4673685A
  申请人：——

  公开号：US4673685A

  公开（公告）日：1987-06-16
• 9,11-Epoxy-9-homo-14-thiaprost-5-enoic acid derivatives: potent thromboxane A2 antagonists
  作者：Steven E. Hall、Wen Ching Han、Don N. Harris、Anders Hedberg、Martin L. Ogletree

  DOI：10.1021/jm00125a009

  日期：1989.5

  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).