methyl <1β,2α(Z),3α,4β>-7-<3-(2-hydroxyethyl)-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoate | 104596-27-2

• 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 <1β,2α(Z),3α,4β>-7-<3-(2-hydroxyethyl)-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoate
• CAS: 104596-27-2
• 化学式: C₁₆H₂₆O₄
• 分子量: 282.38
• InChiKey: PZATUIJSKFLSEE-JPAKQDGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  20.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl <1β,2α(Z),3α,4β>-7-<3-(2-hydroxyethyl)-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 、 甲醇 、 xylene 为溶剂， 生成 <1β,2α(Z),3α,4β>-7-<3-<2-(pentyloxy)ethyl>-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoic acid
  参考文献：
  名称：

  9,11-Epoxy-9-homo-14-oxaprosta-5-enoic acid derivatives. Novel inhibitors of fatty acid cyclooxygenase

  摘要：

  A novel bicyclic prostaglandin analogue, [1R-[l alpha,2 beta (5Z),3 beta,4 alpha]]-7-[3-[(hexyloxy)methyl]- 7-oxabicyclo[2.2.1]hept-2-yl]-5-heptenoic acid (1), and cogeners were found to be potent inhibitors of fatty acid cyclooxygenase. Compound 1 was the only stereoisomer out of eight possible structures that was active. Ether 1 was 20 times more potent than indomethacin (IND) in inhibiting arachidonic acid (AA) induced aggregation of human platelet-rich plasma. Compound 1 was also more potent than IND in several in vivo assays, AA-induced sudden death in the conscious mouse (2 times) and AA-induced bronchoconstriction in the anesthetized guinea pig (16-45 times).

  DOI：

  10.1021/jm00161a032
• 作为产物：
  描述：

  methyl <1S-<1α,2α(Z),3α,4α>>-7-<3-(formylmethyl)-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoate 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以69%的产率得到methyl <1β,2α(Z),3α,4β>-7-<3-(2-hydroxyethyl)-7-oxabicyclo<2.2.1>hept-2-yl>-5-heptenoate
  参考文献：
  名称：

  9,11-Epoxy-9-homo-14-oxaprosta-5-enoic acid derivatives. Novel inhibitors of fatty acid cyclooxygenase

  摘要：

  A novel bicyclic prostaglandin analogue, [1R-[l alpha,2 beta (5Z),3 beta,4 alpha]]-7-[3-[(hexyloxy)methyl]- 7-oxabicyclo[2.2.1]hept-2-yl]-5-heptenoic acid (1), and cogeners were found to be potent inhibitors of fatty acid cyclooxygenase. Compound 1 was the only stereoisomer out of eight possible structures that was active. Ether 1 was 20 times more potent than indomethacin (IND) in inhibiting arachidonic acid (AA) induced aggregation of human platelet-rich plasma. Compound 1 was also more potent than IND in several in vivo assays, AA-induced sudden death in the conscious mouse (2 times) and AA-induced bronchoconstriction in the anesthetized guinea pig (16-45 times).

  DOI：

  10.1021/jm00161a032

文献信息

• 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).