5E-9a-carba-14(1-hydroxy-4-isopropylidenecyclohexyl)-13,14-dehydro prostaglandin I₂ | 142076-66-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 5E-9a-carba-14(1-hydroxy-4-isopropylidenecyclohexyl)-13,14-dehydro prostaglandin I₂
• 英文别名: (5E)-5-[(3aS,4S,5R,6aS)-5-hydroxy-4-[2-(1-hydroxy-4-propan-2-ylidenecyclohexyl)ethynyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid
• CAS: 142076-66-2；142076-67-3
• 化学式: C₂₄H₃₄O₄
• 分子量: 386.532
• InChiKey: CDGLOCLYLYWRFA-KTWLZQPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ethylene ketal of 2,3-epoxy-bicyclo<3.3.0>octane-7-one 在 正丁基锂 、 硫酸 、 三氟化硼乙醚 、 氢气 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 生成 5E-9a-carba-14(1-hydroxy-4-isopropylidenecyclohexyl)-13,14-dehydro prostaglandin I₂
  参考文献：
  名称：

  Synthesis and anti-aggregative activity of novel ω-achiral carba-analogues of prostacyclin

  摘要：

  Novel stable bicyclo[3.3.0]octanic and bicyclo[4.2.0]octanic 13,14-didehydrocarbacyclins 1a-c, 2a bearing an achiral cyclohexanoic group at C-14 were synthesized. These analogues have been characterized by C-13 NMR spectroscopy. Compounds 1a-c and 2a were tested on rabbit and human platelet-rich blood plasma and 1a-c on rat stomach and guinea pig trachea smooth muscles. E-isomers of 1a-b were found to be less active but more selective than PGE1. The anti-aggregative potency of E-isomer of compounds 1a-b and Z-isomer of 2a on human platelets was 10(-1) - 10(-2) of the activity of PGE1. The contractive activity of bicyclo[3.3.0]octane analogues 1a-c was 10(-3) - 10(-4) of that for PGE1. On platelets and guinea-pig trachea 5E-isomers of the Corresponding analogues were more potent, whereas on rat stomach muscle 5Z-isomers were.

  DOI：

  10.1016/0223-5234(92)90104-9