6-(1-Iodo-2-{(1S,2R,3S,4R)-3-[(E)-(3R,4S)-4-phenyl-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-7-oxa-bicyclo[2.2.1]hept-2-yl}-ethyl)-tetrahydro-pyran-2-one | 104101-46-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡喃类
• 英文名称: 6-(1-Iodo-2-{(1S,2R,3S,4R)-3-[(E)-(3R,4S)-4-phenyl-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-7-oxa-bicyclo[2.2.1]hept-2-yl}-ethyl)-tetrahydro-pyran-2-one
• CAS: 104101-46-4
• 化学式: C₂₉H₃₉IO₅
• 分子量: 594.53
• InChiKey: XYACMDPPUSPFHZ-JVROBXHVSA-N

反应信息

• 作为反应物：
  描述：

  6-(1-Iodo-2-{(1S,2R,3S,4R)-3-[(E)-(3R,4S)-4-phenyl-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-7-oxa-bicyclo[2.2.1]hept-2-yl}-ethyl)-tetrahydro-pyran-2-one 在 lithium hydroxide 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 5,6-Dihydroxy-7-{(1S,2R,3S,4R)-3-[(E)-(3R,4S)-4-phenyl-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-7-oxa-bicyclo[2.2.1]hept-2-yl}-heptanoic 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
• 作为产物：
  描述：

  (Z)-7-{(1S,2R,3S,4R)-3-[(E)-(3R,4S)-4-Phenyl-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-7-oxa-bicyclo[2.2.1]hept-2-yl}-hept-5-enoic acid 在 碘 、 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 6-(1-Iodo-2-{(1S,2R,3S,4R)-3-[(E)-(3R,4S)-4-phenyl-3-(tetrahydro-pyran-2-yloxy)-pent-1-enyl]-7-oxa-bicyclo[2.2.1]hept-2-yl}-ethyl)-tetrahydro-pyran-2-one
  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