methyl (4aS,4bR,10aR,10bS,12aS)-10a,12a-dimethyl-2-oxo-1,2,3,4,4a,4b,5,9,10,10a,10b,11,12,12a-tetradecahydronaphtho[2,1-f]quinoline-8-carboxylate | 1266250-81-0

• 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: methyl (4aS,4bR,10aR,10bS,12aS)-10a,12a-dimethyl-2-oxo-1,2,3,4,4a,4b,5,9,10,10a,10b,11,12,12a-tetradecahydronaphtho[2,1-f]quinoline-8-carboxylate
• CAS: 1266250-81-0
• 化学式: C₂₁H₂₉NO₃
• 分子量: 343.466
• InChiKey: JVQYGSAFDPDUJL-OZMCLOMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  25.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl (4aS,4bR,10aR,10bS,12aS)-10a,12a-dimethyl-2-oxo-1,2,3,4,4a,4b,5,9,10,10a,10b,11,12,12a-tetradecahydronaphtho[2,1-f]quinoline-8-carboxylate 在 水 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 以98%的产率得到17a-aza-17-oxo-17a-homoandrosta-3,5-dien-3-oic acid
  参考文献：
  名称：

  Discovery of a novel hybrid from finasteride and epristeride as 5α-reductase inhibitor

  摘要：

  Finasteride and epristeride both inhibit 5 alpha-reductase with high potency via competitive and non-competitive mechanism, respectively. A new hybrid of finasteride and epristeride was designed as a new 5a-reductase inhibitor based on combination principles in medicinal chemistry. Human 5 beta-reductase was chosen as a plausible surrogate of 5 alpha-reductase type II and the results indicate that although the hybrid compound possesses the main bulk of epristeride, its inhibitory mechanism is same as of finasteride. The hybrid turned out to be a potent 5 alpha-reductase inhibitor in low IC50 ranges. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2010.10.112
• 作为产物：
  描述：

  C₂₁H₂₉NO₃ 在 氯化亚砜 作用下， 以 1,4-二氧六环 为溶剂， 以83%的产率得到methyl (4aS,4bR,10aR,10bS,12aS)-10a,12a-dimethyl-2-oxo-1,2,3,4,4a,4b,5,9,10,10a,10b,11,12,12a-tetradecahydronaphtho[2,1-f]quinoline-8-carboxylate
  参考文献：
  名称：

  Discovery of a novel hybrid from finasteride and epristeride as 5α-reductase inhibitor

  摘要：

  Finasteride and epristeride both inhibit 5 alpha-reductase with high potency via competitive and non-competitive mechanism, respectively. A new hybrid of finasteride and epristeride was designed as a new 5a-reductase inhibitor based on combination principles in medicinal chemistry. Human 5 beta-reductase was chosen as a plausible surrogate of 5 alpha-reductase type II and the results indicate that although the hybrid compound possesses the main bulk of epristeride, its inhibitory mechanism is same as of finasteride. The hybrid turned out to be a potent 5 alpha-reductase inhibitor in low IC50 ranges. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2010.10.112