16β,17β-epoxymethyleneandrost-5-ene-3β-ol | 85640-13-7

• 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: 16β,17β-epoxymethyleneandrost-5-ene-3β-ol
• 英文别名: 17β,16β-epoxymethylenandrost-5-en-3β-ol
• CAS: 85640-13-7
• 化学式: C₂₀H₃₀O₂
• 分子量: 302.457
• InChiKey: GVJSPTQSKGABPA-PFCIIFMMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.94
• 重原子数：
  22.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  16β,17β-epoxymethyleneandrost-5-ene-3β-ol 在 环己酮 、 aluminum isopropoxide 作用下， 以 甲苯 为溶剂， 反应 5.0h， 生成 17β,16β-epoxymethylenandrost-4-en-3-one
  参考文献：
  名称：

  In vitro inhibitory effects of 16-methyl-substituted steroids on 5α-reductase in rat and human prostates

  摘要：

  The inhibitory effects (IC50) of 16-methyl steroids on 5 alpha-reductase were studied. The in vitro experiments were carried out with homogenates of rat and human prostates. The investigated 16-methyl steroids were found to be weak inhibitors. In comparison with the known 5 alpha-reductase inhibitor 4-MA (17 beta-N, N-diethylcarbamol-4-methyl-4-aza-5 alpha-androstan-3-one), the relative IC50 values of the studied compounds are 4.7 times or more greater than 4-MA in human prostate and 23.5 times or more greater than 4-MA in rat prostate. The IC50 values increase in the sequence 16 alpha-, 16 beta- and 16,16-dimethyl derivatives. In human prostate homogenates IC50 caries between 0.6 and 120, while in rat it ranges from 1.6 to 1000 mu M. This shows that the enzyme of the human prostate is more sensitive than that of the rat prostate to the methyl-substituted compounds.

  DOI：

  10.1016/0039-128x(94)90049-3
• 作为产物：
  描述：

  16β-hydroxymethylandrost-5-ene-3β,17β-diol 3-acetate 在 吡啶 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 16β,17β-epoxymethyleneandrost-5-ene-3β-ol
  参考文献：
  名称：

  Schneider; Vincze; Hackler, Acta Chimica Academiae Scientiarum Hungaricae, 1982, vol. 110, # 4, p. 429 - 440

  摘要：

  DOI：