methyl 17-(N-tert-butylcarbamoyl)estra-1,3,5(10),16-tetraene-3-carboxylate | 124651-19-0

• 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 17-(N-tert-butylcarbamoyl)estra-1,3,5(10),16-tetraene-3-carboxylate
• 英文别名: methyl (8S,9S,13S,14S)-17-(tert-butylcarbamoyl)-13-methyl-6,7,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthrene-3-carboxylate
• CAS: 124651-19-0
• 化学式: C₂₅H₃₃NO₃
• 分子量: 395.542
• InChiKey: HWXGTWLTHZOXQI-PUFAWVJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.78
• 重原子数：
  29.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 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 17-(N-tert-butylcarbamoyl)estra-1,3,5(10),16-tetraene-3-carboxylate 在 platinum(IV) oxide 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 3.0h， 生成 3-(methoxycarbonyl)estra-1,3,5(10)-triene-17β-carboxylic acid tert-butylamide
  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：

  3,17-bis-(trifluoromethylsulfonyloxy)-13β-estra-1,3,5(10),16-tetraene 在 palladium diacetate 、 1,3-双(二苯基膦)丙烷 、 三乙胺 、 三苯基膦 作用下， 以 二甲基亚砜 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 methyl 17-(N-tert-butylcarbamoyl)estra-1,3,5(10),16-tetraene-3-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