N-diphenylmethyl-3,11-dioxo-4-methyl-4-aza-5α-androstane-17β-carboxamide | 152398-89-5

• 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: N-diphenylmethyl-3,11-dioxo-4-methyl-4-aza-5α-androstane-17β-carboxamide
• 英文别名: (1S,3aS,3bS,5aR,9aR,9bS,11aS)-N-benzhydryl-6,9a,11a-trimethyl-7,10-dioxo-1,2,3,3a,3b,4,5,5a,8,9,9b,11-dodecahydroindeno[5,4-f]quinoline-1-carboxamide
• CAS: 152398-89-5
• 化学式: C₃₃H₄₀N₂O₃
• 分子量: 512.692
• InChiKey: XOFPFYWRNRVXEZ-HNKAIJPBSA-N

物化性质

• 沸点：
  722.5±60.0 °C(predicted)
• 密度：
  1.157±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  38
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  66.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-diphenylmethyl-3,11-dioxo-4-methyl-4-aza-5α-androstane-17β-carboxamide 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以96%的产率得到N-diphenylmethyl-11β-hydroxy-4-methyl-3-oxo-4-aza-5α-androstane-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 、 氰基磷酸二乙酯 、 potassium tert-butylate 、 氨 、 氢气 、 碘 、 sodium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙二醇 、 溶剂黄146 、 丙酮 、 叔丁醇 为溶剂， 反应 63.75h， 生成 N-diphenylmethyl-3,11-dioxo-4-methyl-4-aza-5α-androstane-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

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.