2β-(morpholin-4-yl)-5α-androstane-3α,17β-diol | 981-50-0

• 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: 2β-(morpholin-4-yl)-5α-androstane-3α,17β-diol
• 英文别名: 2β-Morpholino-5α-androstan-3α,17β-diol；2-morpholin-4-yl-androstane-3,17-diol；(2S,3S,5S,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-2-morpholin-4-yl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol
• CAS: 981-50-0
• 化学式: C₂₃H₃₉NO₃
• 分子量: 377.568
• InChiKey: YZEMCBKOBHYVHA-NQBGTIOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  52.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2β-(morpholin-4-yl)-5α-androstane-3α,17β-diol 生成 Di-O-acetyl-2β-morpholino-5α-androstan-3α,17β-diol
  参考文献：
  名称：

  氨基类固醇。第三部分 2-和3-氨基5α-雄烷

  摘要：

  2α，3α-和2β，3β-环氧-5α-雄烷酮与仲环胺的缩合分别得到2β-氨基-3α-醇和3α-氨基-2β-醇。2β-溴-3α-羟基-5α-雄甾烷与相同的环胺反应生成2α，3α-环氧化合物，与3α-溴-2β-羟基异构体相反，该取代基不经转化即得到相应的3α -氨基-2β-醇。讨论了这些反应的机理。还描述了2-吗啉代-5α-雄烷-1-烯-3，17-二酮的制备。

  DOI：

  10.1039/j39680001134
• 作为产物：
  描述：

  吗啉 、 2-羧基阿拉伯糖醇1-磷酸酯 以 水 为溶剂， 反应 24.0h， 生成 2β-(morpholin-4-yl)-5α-androstane-3α,17β-diol
  参考文献：
  名称：

  Chemical synthesis of 2β-amino-5α-androstane-3α,17β-diol N-derivatives and their antiproliferative effect on HL-60 human leukemia cells

  摘要：

  Even though few steroids are used for the treatment of leukemia, 2 beta-(4-methylpiperazinyl)-5 alpha-androstane-3 alpha,17 beta-diol (1) was recently reported for its ability to inhibit the proliferation of human leukemia HL-60 cells. With an efficient procedure that we had developed for the aminolysis of hindered steroidal epoxides, we synthesized a series of 2 beta-amino-5 alpha-androstane-3 alpha,17 beta-diol N-derivatives structurally similar to 1. Hence, the opening of 2,3 alpha-epoxy-5 alpha-androstan-17 beta-diol with primary and secondary amines allowed the synthesis of aminosteroids with diverse length, rami. cation, and functionalization of the 2 beta-side chain. Sixty-four steroid derivatives were tested for their capacity to inhibit the proliferation of HL-60 cells; thus obtaining first structure - activity relationship results. Ten aminosteroids with long alkyl chains (7 - 16 carbons) or bulky groups (diphenyl or adamantyl) have shown antiproliferative activity over 78% at 10 mu M and superior to that of the lead compound. The 3,3-diphenylpropylamino, 4-nonylpiperazinyl and octylamino derivatives of 5 alpha-androstane-3 alpha,17 beta-diol inhibited the HL-60 cell growth with IC(50) of 3.1, 4.2 and 6.4 mu M, respectively. They were also found to induce the HL-60 cell differentiation. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.03.031

文献信息

• Chemical synthesis of 2β-amino-5α-androstane-3α,17β-diol N-derivatives and their antiproliferative effect on HL-60 human leukemia cells
  作者：Dominic Thibeault、Jenny Roy、Patrick DeRoy、Donald Poirier

  DOI：10.1016/j.bmc.2008.03.031

  日期：2008.5

  Even though few steroids are used for the treatment of leukemia, 2 beta-(4-methylpiperazinyl)-5 alpha-androstane-3 alpha,17 beta-diol (1) was recently reported for its ability to inhibit the proliferation of human leukemia HL-60 cells. With an efficient procedure that we had developed for the aminolysis of hindered steroidal epoxides, we synthesized a series of 2 beta-amino-5 alpha-androstane-3 alpha,17 beta-diol N-derivatives structurally similar to 1. Hence, the opening of 2,3 alpha-epoxy-5 alpha-androstan-17 beta-diol with primary and secondary amines allowed the synthesis of aminosteroids with diverse length, rami. cation, and functionalization of the 2 beta-side chain. Sixty-four steroid derivatives were tested for their capacity to inhibit the proliferation of HL-60 cells; thus obtaining first structure - activity relationship results. Ten aminosteroids with long alkyl chains (7 - 16 carbons) or bulky groups (diphenyl or adamantyl) have shown antiproliferative activity over 78% at 10 mu M and superior to that of the lead compound. The 3,3-diphenylpropylamino, 4-nonylpiperazinyl and octylamino derivatives of 5 alpha-androstane-3 alpha,17 beta-diol inhibited the HL-60 cell growth with IC(50) of 3.1, 4.2 and 6.4 mu M, respectively. They were also found to induce the HL-60 cell differentiation. (c) 2008 Elsevier Ltd. All rights reserved.
• Amino-steroids. Part III. 2- and 3-Amino-5α-androstanes
  作者：C. L. Hewett、D. S. Savage

  DOI：10.1039/j39680001134

  日期：——

  Condensation of 2α,3α- and 2β,3β-epoxy-5α-androstanes with secondary cyclic amines gives 2β-amino-3α-ols and 3α-amino-2β-ols respectively; reaction of a 2β-bromo-3α-hydroxy-5α-androstane with the same cyclic amines gives the 2α,3α-epoxide in contrast to the 3α-bromo-2β-hydroxy-isomer, which undergoes substitution without inversion to give the corresponding 3α-amino-2β-ol. The mechanisms of these reactions

  2α，3α-和2β，3β-环氧-5α-雄烷酮与仲环胺的缩合分别得到2β-氨基-3α-醇和3α-氨基-2β-醇。2β-溴-3α-羟基-5α-雄甾烷与相同的环胺反应生成2α，3α-环氧化合物，与3α-溴-2β-羟基异构体相反，该取代基不经转化即得到相应的3α -氨基-2β-醇。讨论了这些反应的机理。还描述了2-吗啉代-5α-雄烷-1-烯-3，17-二酮的制备。