<3aS-<2E,3aα,4α(1Z,3S)-5β,6aα>>-5--2(1H)-pentalenylidene>pentanoic acid methyl ester | 116679-46-0

• 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: <3aS-<2E,3aα,4α(1Z,3S)-5β,6aα>>-5--2(1H)-pentalenylidene>pentanoic acid methyl ester
• 英文别名: methyl (5E)-5-[(3aS,4S,5R,6aS)-4-[(Z,3S)-2-chloro-3-(2,3-dihydro-1H-inden-2-yl)-3-hydroxyprop-1-enyl]-5-hydroxy-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoate
• CAS: 116679-46-0
• 化学式: C₂₆H₃₃ClO₄
• 分子量: 444.999
• InChiKey: UZXFPBQFHNTSHA-JIJVVZFZSA-N

物化性质

• 沸点：
  577.2±50.0 °C(predicted)
• 密度：
  1.294±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.56
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  66.76
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  <3aS-<2E,3aα,4α(1Z,3S)-5β,6aα>>-5--2(1H)-pentalenylidene>pentanoic acid methyl ester 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 10.0h， 以79%的产率得到<3aS-<2E,3aα,4α(3R),5β,6aα>>-5--2(1H)-pentalenylidene>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
• 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 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

文献信息

• TSUYOSHI, TOMIYAMA;SHUICHI, WAKABAYASHI;MASAYUKI, YOKOTA, J. MED. CHEM., 32,(1989) N, C. 1988-1996
  作者：TSUYOSHI, TOMIYAMA、SHUICHI, WAKABAYASHI、MASAYUKI, YOKOTA

  DOI：——

  日期：——