5-[(3aS,4R,5R,6aS)-4-((E)-(R)-3-Benzo[1,3]dioxol-5-yl-3-hydroxy-propenyl)-5-hydroxy-hexahydro-pentalen-(2E)-ylidene]-pentanoic acid | 116679-30-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 5-[(3aS,4R,5R,6aS)-4-((E)-(R)-3-Benzo[1,3]dioxol-5-yl-3-hydroxy-propenyl)-5-hydroxy-hexahydro-pentalen-(2E)-ylidene]-pentanoic acid
• CAS: 116679-30-2
• 化学式: C₂₃H₂₈O₆
• 分子量: 400.472
• InChiKey: MEOIIKOGHGNDTH-APCIGGKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  96.22
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-[(3aS,4R,5R,6aS)-4-((E)-(R)-3-Benzo[1,3]dioxol-5-yl-3-hydroxy-propenyl)-5-hydroxy-hexahydro-pentalen-(2E)-ylidene]-pentanoic acid 在 sodium tetrahydroborate 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 15.58h， 生成 <3aS-<2E,3aα,4α(1Z,3S)-5β,6aα>>-5--2(1H)-pentalenylidene>pentanoic acid methyl ester
  参考文献：
  名称：

  Synthesis and biological activity of novel carbacyclins having bicyclic substituents on the .omega.-chain

  摘要：

  A number of carbacyclins having bicyclic substituents on the omega-chain have been synthesized and tested for antiplatelet aggregation activity in vitro (against collagen-induced aggregation of rat platelet), for reduction of systemic blood pressure in vivo (ability to reduce the blood pressure in anesthetized rat by iv injection), and for cytoprotective activity (protection against ethanol-induced rat gastric lesion). The most effective compound for each activity was [3aS-[2E,3a alpha,4 alpha (3R),5 beta,6a alpha]]-5-[hexahydro-5- hydroxy-4-[3-hydroxy-3-(2-indanyl)-1-propynyl]-2(1H)-pentalenylidene+ ++] pentanoic acid (compound 11a), while some 1,4-benzodioxan analogues had selectivity for organ-protective activity, and indan analogues showed selectivity in their antiaggregation activity.

  DOI：

  10.1021/jm00128a049
• 作为产物：
  描述：

  5-[(3aS,4R,5R,6aS)-4-((E)-(R)-3-Benzo[1,3]dioxol-5-yl-3-hydroxy-propenyl)-5-hydroxy-hexahydro-pentalen-(2E)-ylidene]-pentanoic acid tert-butyl ester 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 5-[(3aS,4R,5R,6aS)-4-((E)-(R)-3-Benzo[1,3]dioxol-5-yl-3-hydroxy-propenyl)-5-hydroxy-hexahydro-pentalen-(2E)-ylidene]-pentanoic acid
  参考文献：
  名称：

  Synthesis and biological activity of novel carbacyclins having bicyclic substituents on the .omega.-chain

  摘要：

  A number of carbacyclins having bicyclic substituents on the omega-chain have been synthesized and tested for antiplatelet aggregation activity in vitro (against collagen-induced aggregation of rat platelet), for reduction of systemic blood pressure in vivo (ability to reduce the blood pressure in anesthetized rat by iv injection), and for cytoprotective activity (protection against ethanol-induced rat gastric lesion). The most effective compound for each activity was [3aS-[2E,3a alpha,4 alpha (3R),5 beta,6a alpha]]-5-[hexahydro-5- hydroxy-4-[3-hydroxy-3-(2-indanyl)-1-propynyl]-2(1H)-pentalenylidene+ ++] pentanoic acid (compound 11a), while some 1,4-benzodioxan analogues had selectivity for organ-protective activity, and indan analogues showed selectivity in their antiaggregation activity.

  DOI：

  10.1021/jm00128a049