3β-O-(1,2-dipalmitoyl-sn-glycero-3-phospho)-7α-hydroxy-androst-5-en-17-one | 1256087-93-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3β-O-(1,2-dipalmitoyl-sn-glycero-3-phospho)-7α-hydroxy-androst-5-en-17-one
• 英文别名: DPP-7α-OH-DHEA；[(2R)-2-hexadecanoyloxy-3-[hydroxy-[[(3S,7S,8R,9S,10R,13S,14S)-7-hydroxy-10,13-dimethyl-17-oxo-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl]oxy]phosphoryl]oxypropyl] hexadecanoate
• CAS: 1256087-93-0
• 化学式: C₅₄H₉₅O₁₀P
• 分子量: 935.316
• InChiKey: VSJKIMXUKANTNR-JFETVBRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.9
• 重原子数：
  65
• 可旋转键数：
  38
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  146
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  1,2-dipalmitoyl-sn-glycero-3-phosphatidic acid pyridinium salt 、 7-羟基去氢表雄酮 在 吡啶 、 N,N'-二环己基碳二亚胺 作用下， 反应 48.0h， 以57%的产率得到3β-O-(1,2-dipalmitoyl-sn-glycero-3-phospho)-7α-hydroxy-androst-5-en-17-one
  参考文献：
  名称：

  Synthesis of dehydroepiandrosterone analogues modified with phosphatidic acid moiety

  摘要：

  Dehydroepiandrosterone (DHEA) and its metabolite 7 alpha-OH DHEA have many diverse physiological, biological and biochemical effects encompassing various cell types, tissues and organs. In in vitro studies, DHEA analogues have myriad biological actions, but in vivo, especially in oral administration, DHEA produces far more limited clinical effects. One of the possible solutions of this problem is conversion of DHEA to active analogues and/or its transformation into prodrug form. In this article, the studies on the conversion of DHEA and 7 alpha-OH DHEA into their phosphatides by the phosphodiester approach are described. In this esterification, N,N-dicyclohexylcarbodiimide (DCC) was the most efficient coupling agent as well as p-toluenesulphonyl chloride (TsCl). (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2010.08.001

文献信息

• Synthesis of dehydroepiandrosterone analogues modified with phosphatidic acid moiety
  作者：Damian A. Smuga、Małgorzata Smuga、Alina Świzdor、Anna Panek、Czesław Wawrzeńczyk

  DOI：10.1016/j.steroids.2010.08.001

  日期：2010.12

  Dehydroepiandrosterone (DHEA) and its metabolite 7 alpha-OH DHEA have many diverse physiological, biological and biochemical effects encompassing various cell types, tissues and organs. In in vitro studies, DHEA analogues have myriad biological actions, but in vivo, especially in oral administration, DHEA produces far more limited clinical effects. One of the possible solutions of this problem is conversion of DHEA to active analogues and/or its transformation into prodrug form. In this article, the studies on the conversion of DHEA and 7 alpha-OH DHEA into their phosphatides by the phosphodiester approach are described. In this esterification, N,N-dicyclohexylcarbodiimide (DCC) was the most efficient coupling agent as well as p-toluenesulphonyl chloride (TsCl). (C) 2010 Elsevier Inc. All rights reserved.