17β-(N,N-diisopropylcarbamoyl)-4-cyanoestra-1,3,5(10)-triene-3-carboxylic acid | 124651-11-2

• 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)-4-cyanoestra-1,3,5(10)-triene-3-carboxylic acid
• 英文别名: (8S,9S,13S,14S,17S)-4-cyano-17-[di(propan-2-yl)carbamoyl]-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3-carboxylic acid
• CAS: 124651-11-2
• 化学式: C₂₇H₃₆N₂O₃
• 分子量: 436.594
• InChiKey: RDMOHBOLNXOXOL-FEBXYHBTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  81.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  methyl 17β-(N,N-diisopropylcarbamoyl)-4-cyanoestra-1,3,5(10)-triene-3-carboxylate 在 水 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 17β-(N,N-diisopropylcarbamoyl)-4-cyanoestra-1,3,5(10)-triene-3-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

文献信息

• Steroidal A ring aryl carboxylic acids: a new class of steroid 5.alpha.-reductase inhibitors
  作者：Dennis A. Holt、Mark A. Levy、David L. Ladd、Hye Ja Oh、Jill M. Erb、Julie I. Heaslip、Martin Brandt、Brian W. Metcalf

  DOI：10.1021/jm00165a009

  日期：1990.3

  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.