Acetic acid (3S,7S,8R,9S,10R,13S,14S,16R)-16-acetoxy-7-bromo-10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester | 165181-91-9

• 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: Acetic acid (3S,7S,8R,9S,10R,13S,14S,16R)-16-acetoxy-7-bromo-10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester
• CAS: 165181-91-9
• 化学式: C₂₃H₃₁BrO₅
• 分子量: 467.4
• InChiKey: YUCALQAOXMFESG-HUCPXYKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.37
• 重原子数：
  29.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  69.67
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (3S,7S,8R,9S,10R,13S,14S,16R)-16-acetoxy-7-bromo-10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 在 silver(I) acetate 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 2.5h， 生成 3β,7α,17β-trihydroxyandrost-5-en-16-one
  参考文献：
  名称：

  Ergosteroids II: Biologically Active Metabolites and Synthetic Derivatives of Dehydroepiandrosterone 11This work was supported by Humanetics Corp., St. Louis Park, Minnesota.

  摘要：

  An improved procedure for the synthesis of 3 beta-hydroxyandrost-5-ene-7, 17-dione, a natural metabolite of dehydroepiandrosterone (DHEA) is described. The synthesis and magnetic resonance spectra of several other related steroids are presented. Feeding dehydroepiandrosterone to rats induces enhanced formation of several liver enzymes among which are mitochondrial sn-glycerol 3-phosphate dehydrogenase (GPDH) and cytosolic malic enzyme. The induction of these two enzymes, that complete a thermogenic system in rat liver, was used as an assay to search for derivatives of DHEA that might be more active than the parent steroid. Activity is retained in steroids that are reduced to the corresponding 17 beta-hydroxy derivative, or hydroxylated at 7 alpha or 7 beta, and is considerably enhanced when the 17-hydroxy or 17-carbonyl steroid is converted to the 7-oxo derivative. Several derivatives of DHEA did not induce the thermogenic enzymes whereas the corresponding 7-oxo compounds did. Both short and long chain acyl esters of DHEA and of 7-oxo-DHEA are active inducers of the liver enzymes when fed to rats. 7-Oxo-DHEA-3-sulfate is as active as 7-oxo-DHEA or its 3-acetyl ester, whereas DHEA-3-sulfate is much less active than DHEA. Among many steroids tested, those posessing a carbonyl group at position 3, a methyl group at 7, a hydroxyl group at positions 1, 2, 4, 11, or 19, or a saturated B ring, with or without a 4-5 double bond, were inactive. (C) 1998 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(97)00159-1
• 作为产物：
  描述：

  (3B,16A)-3,16-二羟基-雄甾-5-烯-17-酮 在 吡啶 、 1,3-二溴-5,5-二甲基海因 、 碳酸氢钠 、 lithium bromide 作用下， 以 正己烷 、 丙酮 、 甲苯 为溶剂， 反应 12.5h， 生成 Acetic acid (3S,7S,8R,9S,10R,13S,14S,16R)-16-acetoxy-7-bromo-10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester
  参考文献：
  名称：

  Ergosteroids II: Biologically Active Metabolites and Synthetic Derivatives of Dehydroepiandrosterone 11This work was supported by Humanetics Corp., St. Louis Park, Minnesota.

  摘要：

  An improved procedure for the synthesis of 3 beta-hydroxyandrost-5-ene-7, 17-dione, a natural metabolite of dehydroepiandrosterone (DHEA) is described. The synthesis and magnetic resonance spectra of several other related steroids are presented. Feeding dehydroepiandrosterone to rats induces enhanced formation of several liver enzymes among which are mitochondrial sn-glycerol 3-phosphate dehydrogenase (GPDH) and cytosolic malic enzyme. The induction of these two enzymes, that complete a thermogenic system in rat liver, was used as an assay to search for derivatives of DHEA that might be more active than the parent steroid. Activity is retained in steroids that are reduced to the corresponding 17 beta-hydroxy derivative, or hydroxylated at 7 alpha or 7 beta, and is considerably enhanced when the 17-hydroxy or 17-carbonyl steroid is converted to the 7-oxo derivative. Several derivatives of DHEA did not induce the thermogenic enzymes whereas the corresponding 7-oxo compounds did. Both short and long chain acyl esters of DHEA and of 7-oxo-DHEA are active inducers of the liver enzymes when fed to rats. 7-Oxo-DHEA-3-sulfate is as active as 7-oxo-DHEA or its 3-acetyl ester, whereas DHEA-3-sulfate is much less active than DHEA. Among many steroids tested, those posessing a carbonyl group at position 3, a methyl group at 7, a hydroxyl group at positions 1, 2, 4, 11, or 19, or a saturated B ring, with or without a 4-5 double bond, were inactive. (C) 1998 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(97)00159-1