17β-(N,N-diisopropylcarbamoyl)-3-methoxyestra-1,3,5(10)-triene-2-carboxylic acid | 124651-30-5

• 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: 17β-(N,N-diisopropylcarbamoyl)-3-methoxyestra-1,3,5(10)-triene-2-carboxylic acid
• CAS: 124651-30-5
• 化学式: C₂₇H₃₉NO₄
• 分子量: 441.611
• InChiKey: ODFUZDKCWKZYHC-FHSJTRONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.51
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  66.84
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  17β-(N,N-diisopropylcarbamoyl)-3-methoxyestra-1,3,5(10)-triene-2-carboxylic acid 在 三溴化硼 、 sodium hydride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 methyl 3-<<(trifluoromethyl)sulfonyl>oxy>-17β-(N,N-diisopropylcarbamoyl)estra-1,3,5(10)-triene-2-carboxylate
  参考文献：
  名称：

  Steroidal A ring aryl carboxylic acids: a new class of steroid 5.alpha.-reductase inhibitors

  摘要：

  A series of 17 beta-carbamoyl-1,3,5(10)-estratriene-3-carboxylic acids has been prepared and evaluated in vitro as inhibitors of human and rat prostatic steroid 5 alpha-reductase (EC 1.3.1.30). Potent inhibition of the human enzyme, in particular, was observed and preliminary studies using rat enzyme suggest that the inhibition results from the formation of an enzyme-NADP(+)-inhibitor complex. The compounds were synthesized from estrone, generally employing a differentiated bis-triflate carbonylation strategy.

  DOI：

  10.1021/jm00165a009
• 作为产物：
  描述：

  3-甲氧基雌酮 在 platinum(IV) oxide palladium diacetate 、 正丁基锂 、 2,6-二叔丁基-4-甲基吡啶 、 氢气 、 溴 、 三溴化硼 、 potassium carbonate 、 三苯基膦 作用下， 以 乙醇 、 二氯甲烷 、 溶剂黄146 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 17.91h， 生成 17β-(N,N-diisopropylcarbamoyl)-3-methoxyestra-1,3,5(10)-triene-2-carboxylic acid
  参考文献：
  名称：

  Steroidal A ring aryl carboxylic acids: a new class of steroid 5.alpha.-reductase inhibitors

  摘要：

  A series of 17 beta-carbamoyl-1,3,5(10)-estratriene-3-carboxylic acids has been prepared and evaluated in vitro as inhibitors of human and rat prostatic steroid 5 alpha-reductase (EC 1.3.1.30). Potent inhibition of the human enzyme, in particular, was observed and preliminary studies using rat enzyme suggest that the inhibition results from the formation of an enzyme-NADP(+)-inhibitor complex. The compounds were synthesized from estrone, generally employing a differentiated bis-triflate carbonylation strategy.

  DOI：

  10.1021/jm00165a009