prostaglandin E2 1,3-bis(nitrooxy)prop-2-yl ester | 189940-83-8

• 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 E2 1,3-bis(nitrooxy)prop-2-yl ester
• 英文别名: Nitroproston；1,3-dinitrooxypropan-2-yl (Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]hept-5-enoate
• CAS: 189940-83-8
• 化学式: C₂₃H₃₆N₂O₁₁
• 分子量: 516.546
• InChiKey: SGMBTYBNUOWYOV-CXZSOYKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  36
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  194
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  在 4-二甲氨基吡啶 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 以134 mg的产率得到prostaglandin E2 1,3-bis(nitrooxy)prop-2-yl ester
  参考文献：
  名称：

  1,3-Dinitrates of cyclooxygenase metabolites of endocannabinoid 2-arachidonoylglycerol. Synthesis and properties

  摘要：

  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.

  DOI：

  10.1134/s1068162009020113

文献信息

• Prostaglandin fluorides in synthesis of natural prostaglandin derivatives at carboxyl group
  作者：I. V. Serkov、V. V. Bezuglov

  DOI：10.1134/s1068162009010142

  日期：2009.1

  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.
• REMEDY FOR HAIR GROWTH ENHANCING
  申请人：REGEUS LIMITED LIABILITY COMPANY

  公开号：US20220249514A1

  公开（公告）日：2022-08-11

  The invention relates to the field of cosmetology, dermatology and medicine, and is concerned with the development and production of a combination, and also of a composition based thereon, for hair growth enhancing in mammals and/or for preventing and/or treating alopecia, primarily in humans, and more particularly to combinations based on derivatives of F- and E-type prostaglandins, characterized by the absence of undesirable side-effects, and also to a stable composition comprising said combination. The use of a combination of prostaglandins in a single composition makes it possible to simultaneously activate a plurality of physiological processes, including stimulating a hair follicle to produce a new hair, increasing the local microcirculation in the area adjacent to the hair follicle, and reducing the aggregation of thrombocytes, thereby preventing thrombogenesis in the capillary network. Furthermore, the presence in the combination or in the composition based thereon of modified prostaglandins carrying a group of nitrogen oxide donors enables better penetration of other ingredients of the combination or composition into the skin.
• 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.