5E-9a-carba-14(1-hydroxycyclohexyl)-13,14-dehydro prostaglandin I₂ | 122976-73-2

• 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-hydroxycyclohexyl)-13,14-dehydro prostaglandin I₂
• 英文别名: (+/-)-13,14-didehydro-15,16,17,18,19,20-hexanor-14-(1-hydroxycyclohexyl)carbacyclin；13,14-dehydro-15-cyclohexyl Carbaprostacyclin；(5E)-5-[(3aS,4S,5R,6aS)-5-hydroxy-4-[2-(1-hydroxycyclohexyl)ethynyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid
• CAS: 122976-73-2；142076-63-9；145375-81-1；145375-82-2；145375-85-5；145375-91-3
• 化学式: C₂₁H₃₀O₄
• 分子量: 346.467
• InChiKey: LGIPMFCHTFFLFR-PRYZLTTQSA-N

物化性质

• 沸点：
  559.9±50.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)
• 溶解度：
  DMF：>10 mg/ml（来自 6B-PGI2）； DMSO：>5 mg/ml（来自 6B-PGI2）；乙醇：>20 mg/ml（来自 6B-PGI2）； PBS pH 7.2：>80 mg/ml（来自 6B-PGI2）

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 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：

  4-carboxybutyliden triphenylphosphorane sodium 在 氢气 作用下， 以 二甲基亚砜 为溶剂， 生成 5E-9a-carba-14(1-hydroxycyclohexyl)-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

文献信息

• Synthesis of a Novel, Optically Active 15-Nonstereogenic Carbaprostacyclin
  作者：Tōnis Kanger、Margus Lopp、Anne Müraus、Madis Lōhmus、Gennadi Kobzar、Tōnis Pehk、Ülo Lille

  DOI：10.1055/s-1992-26262

  日期：——

  Novel, optically active carbacyclin analogues (+)-1 and (-)-1 with an achiral ω-chain were synthesized from homochiral bromohydrins 3a and 4a, respectively.

  分别由纯手性溴醇 3a 和 4a 合成了具有非手性 β 链的新型光学活性碳环素类似物 (+)-1 和 (-)-1。
• Synthesis and anti-aggregative activity of novel ω-achiral carba-analogues of prostacyclin
  作者：M Lopp、G Kobzar、M Bergmann、T Pehk、A Lopp、T Valimäe、M Viigimaa、Ü Lille

  DOI：10.1016/0223-5234(92)90104-9

  日期：1992.3

  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.