2,2-ethylenedioxy-2α-methyl-5α-androstan-17β-ol | 75246-36-5

• 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: 2,2-ethylenedioxy-2α-methyl-5α-androstan-17β-ol
• 英文别名: 17β-hydroxy-2α-methyl-5α-androstan-3-one 3-ethylene ketal；3,3-Aethylendioxy-17β-hydroxy-2α-methyl-5α-androstan；(2R,5S,8R,9S,10S,13S,14S,17S)-2,10,13-trimethylspiro[1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,2'-1,3-dioxolane]-17-ol
• CAS: 75246-36-5
• 化学式: C₂₂H₃₆O₃
• 分子量: 348.526
• InChiKey: CYTLEZJHKQRUMW-NDUYDNQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-ethylenedioxy-2α-methyl-5α-androstan-17β-ol 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到2,2-ethylenedioxy-2α-methyl-5α-androstan-17β-one
  参考文献：
  名称：

  Identification of drostanolone and 17-methyldrostanolone metabolites produced by cryopreserved human hepatocytes

  摘要：

  Methyldrostanolone (2 alpha,17 alpha-dimethyl-17 beta-hydroxy-5 alpha-androstan-3-one) was synthesized from drostanolone (17 beta-hydroxy-2 alpha-methyl-5 alpha-androstan-3-one) and identified in commercial products. Cultures of cryopreserved human hepatocytes were used to study the biotransformation of drostanolone and its 17-methylated derivative. For both steroids, the common 3 alpha-(major) and 3 beta-reduced metabolites were identified by GC-MS analysis of the extracted culture medium and the stereochemistry confirmed by incubation with 3 alpha-hydroxysteroid dehydrogenase. Structures corresponding to hydroxylated metabolites in C-12 (minor) and C-16 were proposed for other metabolites based upon the evaluation of the mass spectra of the pertrimethylsilyl (TMS-d(0) and TMS-d(9)) derivatives. Finally, on the basis of the GC-MS and H-1 NMR data and through chemical synthesis of the 17-methylated model compounds, structures could be proposed for metabolites hydroxylated in C-2. All the metabolites extracted from hepatocyte culture medium were present although in different relative amounts in urines collected following the administration to a human volunteer. therefore confirming the suitability of the cryopreserved hepatocytes to generate characteristic metabolites and study biotransformation of new steroids. (C) 2008 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2008.11.002
• 作为产物：
  描述：

  屈他雄酮 、 乙二醇 在 对甲苯磺酸一水合物 、 原甲酸三乙酯 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到2,2-ethylenedioxy-2α-methyl-5α-androstan-17β-ol
  参考文献：
  名称：

  Identification of drostanolone and 17-methyldrostanolone metabolites produced by cryopreserved human hepatocytes

  摘要：

  Methyldrostanolone (2 alpha,17 alpha-dimethyl-17 beta-hydroxy-5 alpha-androstan-3-one) was synthesized from drostanolone (17 beta-hydroxy-2 alpha-methyl-5 alpha-androstan-3-one) and identified in commercial products. Cultures of cryopreserved human hepatocytes were used to study the biotransformation of drostanolone and its 17-methylated derivative. For both steroids, the common 3 alpha-(major) and 3 beta-reduced metabolites were identified by GC-MS analysis of the extracted culture medium and the stereochemistry confirmed by incubation with 3 alpha-hydroxysteroid dehydrogenase. Structures corresponding to hydroxylated metabolites in C-12 (minor) and C-16 were proposed for other metabolites based upon the evaluation of the mass spectra of the pertrimethylsilyl (TMS-d(0) and TMS-d(9)) derivatives. Finally, on the basis of the GC-MS and H-1 NMR data and through chemical synthesis of the 17-methylated model compounds, structures could be proposed for metabolites hydroxylated in C-2. All the metabolites extracted from hepatocyte culture medium were present although in different relative amounts in urines collected following the administration to a human volunteer. therefore confirming the suitability of the cryopreserved hepatocytes to generate characteristic metabolites and study biotransformation of new steroids. (C) 2008 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2008.11.002

文献信息

• Male contraceptive steroids and methods of use
  申请人：The Upjohn Company

  公开号：US04297350A1

  公开（公告）日：1981-10-27

  The steroids of the present invention have been found to be useful as male contraceptives when administered orally. Upon cessation of administration of the male contraceptive steroids of the present invention the male promptly regains normal fertility.

  本发明的类固醇在口服时被发现可作为男性避孕药物。停止使用本发明的男性避孕类固醇后，男性很快恢复正常生育能力。