3,11-dioxo-4-aza-5α-androst-1-ene-17β-carboxylic acid | 152398-55-5

• 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: 3,11-dioxo-4-aza-5α-androst-1-ene-17β-carboxylic acid
• 英文别名: (1S,3aS,3bS,5aR,9aR,9bS,11aS)-9a,11a-dimethyl-7,10-dioxo-2,3,3a,3b,4,5,5a,6,9b,11-decahydro-1H-indeno[5,4-f]quinoline-1-carboxylic acid
• CAS: 152398-55-5
• 化学式: C₁₉H₂₅NO₄
• 分子量: 331.412
• InChiKey: JFENVTISBDXKLD-LNJNGVFESA-N

物化性质

• 沸点：
  575.3±50.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  83.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,11-dioxo-4-aza-5α-androst-1-ene-17β-carboxylic acid 在 氰基磷酸二乙酯 、 potassium tert-butylate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 31.0h， 生成 N-diphenylmethyl-3,11-dioxo-4-methyl-4-aza-5α-androst-1-ene-17β-carboxamide
  参考文献：
  名称：

  Synthesis and testosterone 5α-reductase inhibitory activity of 11-substituted 4-aza-5α-androstane compounds

  摘要：

  11 alpha-Acetoxy-, 11 alpha-hydroxy-, 11 beta-hydroxy-, and 11-oxo-4-aza-5 alpha-androstane compounds with an N-diphenylmethylcarbamoyl moiety at the C-17 position were synthesized and their inhibitory activities against rat and human testosterone 5 alpha-reductase were tested. Introduction of the 11 alpha-acetoxy, 11 alpha-hydroxy, 11 beta-hydroxy and 11-oxo groups into 4-aza-5 alpha-androstane compounds reduced the inhibitory activity against rat and human 5 alpha-reductase. The 11 alpha-acetoxy-4-aza-5 alpha-androstane compound in particular lost almost all its activity. However, several compounds with an 11 beta-hydroxy or 11-oxo group showed inhibitory activities comparable to MK-906. The 4-methyl-11 beta-hydroxy-4-aza-5a-androstane derivative showed the most potent inhibitory activity against rat and human enzyme, and was more active than MK-906.

  DOI：

  10.1016/0223-5234(96)85876-4
• 作为产物：
  描述：

  11Alpha-孕酮 在 platinum(IV) oxide 吡啶 、 氢氧化钾 、 potassium permanganate 、 sodium periodate 、 jones reagent 、 DDQ副产物 、 氨 、 氢气 、 碘 、 N,O-双(三甲基硅烷基)三氟乙酰胺 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 乙二醇 、 溶剂黄146 、 丙酮 、 叔丁醇 为溶剂， 反应 54.75h， 生成 3,11-dioxo-4-aza-5α-androst-1-ene-17β-carboxylic acid
  参考文献：
  名称：

  Synthesis and testosterone 5α-reductase inhibitory activity of 11-substituted 4-aza-5α-androstane compounds

  摘要：

  11 alpha-Acetoxy-, 11 alpha-hydroxy-, 11 beta-hydroxy-, and 11-oxo-4-aza-5 alpha-androstane compounds with an N-diphenylmethylcarbamoyl moiety at the C-17 position were synthesized and their inhibitory activities against rat and human testosterone 5 alpha-reductase were tested. Introduction of the 11 alpha-acetoxy, 11 alpha-hydroxy, 11 beta-hydroxy and 11-oxo groups into 4-aza-5 alpha-androstane compounds reduced the inhibitory activity against rat and human 5 alpha-reductase. The 11 alpha-acetoxy-4-aza-5 alpha-androstane compound in particular lost almost all its activity. However, several compounds with an 11 beta-hydroxy or 11-oxo group showed inhibitory activities comparable to MK-906. The 4-methyl-11 beta-hydroxy-4-aza-5a-androstane derivative showed the most potent inhibitory activity against rat and human enzyme, and was more active than MK-906.

  DOI：

  10.1016/0223-5234(96)85876-4

文献信息

• Synthesis and testosterone 5α-reductase inhibitory activity of 11-substituted 4-aza-5α-androstane compounds
  作者：K Ishibashi、H Kurata、T Hamada、H Horikoshi、K Kojima

  DOI：10.1016/0223-5234(96)85876-4

  日期：1996.1

  11 alpha-Acetoxy-, 11 alpha-hydroxy-, 11 beta-hydroxy-, and 11-oxo-4-aza-5 alpha-androstane compounds with an N-diphenylmethylcarbamoyl moiety at the C-17 position were synthesized and their inhibitory activities against rat and human testosterone 5 alpha-reductase were tested. Introduction of the 11 alpha-acetoxy, 11 alpha-hydroxy, 11 beta-hydroxy and 11-oxo groups into 4-aza-5 alpha-androstane compounds reduced the inhibitory activity against rat and human 5 alpha-reductase. The 11 alpha-acetoxy-4-aza-5 alpha-androstane compound in particular lost almost all its activity. However, several compounds with an 11 beta-hydroxy or 11-oxo group showed inhibitory activities comparable to MK-906. The 4-methyl-11 beta-hydroxy-4-aza-5a-androstane derivative showed the most potent inhibitory activity against rat and human enzyme, and was more active than MK-906.