prostaglandin F2α 1,3-bis(nitrooxy)prop-2-yl ester | 189940-94-1

• 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: prostaglandin F2α 1,3-bis(nitrooxy)prop-2-yl ester
• 英文别名: 1,3-dinitrooxypropan-2-yl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoate
• CAS: 189940-94-1
• 化学式: C₂₃H₃₈N₂O₁₁
• 分子量: 518.562
• InChiKey: WZDWKQYKULVRLS-PKBBWAGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  36
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  197
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  在 盐酸 、 水 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以115.6 mg的产率得到prostaglandin F2α 1,3-bis(nitrooxy)prop-2-yl ester
  参考文献：
  名称：

  Prostaglandin fluorides in synthesis of natural prostaglandin derivatives at carboxyl group

  摘要：

  Methods of synthesis of prostaglandin fluorides were developed and their properties were investigated. These compounds were shown to be convenient synthetic precursors for obtaining esters and amides of natural prostaglandins and their fluorodeoxy analogues.

  DOI：

  10.1134/s1068162009010142

文献信息

• 1,3-Dinitrates of cyclooxygenase metabolites of endocannabinoid 2-arachidonoylglycerol. Synthesis and properties
  作者：I. V. Serkov、V. V. Bezuglov

  DOI：10.1134/s1068162009020113

  日期：2009.3

  The 1,3-Dinitrates of glycerol esters of natural prostaglandins that are the cyclooxygenase metabolites of 2-arachidonoylglycerol, an endogenous ligand of cannabinoid receptors, were synthesized for the first time. Four methods of synthesis of these esters were developed via the activation of a carboxyl group and their chemical and pharmacological properties were investigated. The esters exhibit a more selective pharmacological spectrum of activities in comparison with the corresponding natural prostaglandins: some types of myotropic activity were enhanced, while others were loosened. 1,3-dinitroglycerol esters act as vasodilators, whereas the majority of natural prostaglandins act as vasoconstrictors. The observed changes result from the introduction of an NO-releasing fragment into prostaglandin molecule.