(8S,9S,13S,14S,17S)-17-[二(丙-2-基)氨基甲酰]-13-甲基-6,7,8,9,11,12,14,15,16,17-十氢环戊烯并[a]菲-3-羧酸 | 124650-99-3

• 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
• 中文名称: (8S,9S,13S,14S,17S)-17-[二(丙-2-基)氨基甲酰]-13-甲基-6,7,8,9,11,12,14,15,16,17-十氢环戊烯并[a]菲-3-羧酸
• 中文别名: 2-丁氧基乙基4-硝基苯酸酯
• 英文名称: 17β-(N,N-diisopropylcarbamoyl)estra-1,3,5(10)-triene-3-carboxylic acid
• 英文别名: 17-(N,N-Diisopropylcarboxamide)estra-1,3,5(10)-triene-3-carboxylic acid；(8S,9S,13S,14S,17S)-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: 124650-99-3
• 化学式: C₂₆H₃₇NO₃
• 分子量: 411.585
• InChiKey: VXKTZBKORWNMBL-OPMJLWCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (8S,9S,13S,14S,17S)-17-[二(丙-2-基)氨基甲酰]-13-甲基-6,7,8,9,11,12,14,15,16,17-十氢环戊烯并[a]菲-3-羧酸 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成
  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：

  雌酚酮 在 platinum(IV) oxide palladium diacetate 、 2,6-二叔丁基-4-甲基吡啶 、 1,3-双(二苯基膦)丙烷 、 水 、 氢气 、 potassium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 二甲基亚砜 、 乙酸乙酯 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.0h， 生成 (8S,9S,13S,14S,17S)-17-[二(丙-2-基)氨基甲酰]-13-甲基-6,7,8,9,11,12,14,15,16,17-十氢环戊烯并[a]菲-3-羧酸
  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

• HOLT, DENNIS A.;LEVY, MARK A.;YEN, HWA-KWO;OH, HYE-JA;METCALF, BRIAN W.;W+, BIOORG. AND MED. CHEM. LETT., 1,(1991) N, C. 27-32
  作者：HOLT, DENNIS A.、LEVY, MARK A.、YEN, HWA-KWO、OH, HYE-JA、METCALF, BRIAN W.、W+

  DOI：——

  日期：——
• 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.