methyl 17β-(N,N-diisopropylcarbamoyl)-3-hydroxyestra-1,3,5(10)-triene-2-carboxylate | 124651-32-7

• 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 17β-(N,N-diisopropylcarbamoyl)-3-hydroxyestra-1,3,5(10)-triene-2-carboxylate
• 英文别名: N,N-diisopropyl-2-carbomethoxy-estr-1,3,5(10)-triene-3-ol-17β-carboxamide；methyl (8S,9S,13S,14S,17S)-17-[di(propan-2-yl)carbamoyl]-3-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-2-carboxylate
• CAS: 124651-32-7
• 化学式: C₂₇H₃₉NO₄
• 分子量: 441.611
• InChiKey: WMBIXKKKLHEIHN-FHSJTRONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 17β-(N,N-diisopropylcarbamoyl)-3-hydroxyestra-1,3,5(10)-triene-2-carboxylate 在 palladium diacetate 、 1,3-双(二苯基膦)丙烷 、 sodium hydride 、 三乙胺 作用下， 以 二甲基亚砜 、 1,2-二氯乙烷 为溶剂， 反应 9.5h， 生成 dimethyl 17β-(N,N-diisopropylcarbamoyl)estra-1,3,5(10)-triene-2,3-dicarboxylate
  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 乙醚 、 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 20.41h， 生成 methyl 17β-(N,N-diisopropylcarbamoyl)-3-hydroxyestra-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

文献信息

• Aromatic steroid 5-alpha-reductase inhibitors
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0343954B1

  公开（公告）日：1994-11-30
• US4954446A
  申请人：——

  公开号：US4954446A

  公开（公告）日：1990-09-04
• [EN] AROMATIC STEROID 5-(ALPHA)-REDUCTASE INHIBITORS
  申请人：SMITHKLINE BECKMAN CORPORATION

  公开号：WO1989011282A1

  公开（公告）日：1989-11-30

  (EN) Invented are substituted acrylate analogues of steroidal synthetic compounds, pharmaceutical compositions containing the compounds, and methods of using these compounds to inhibit steroid 5-$g(a)-reductase including using these compounds to reduce prostate size. Also invented are intermediates used in preparing these compounds.(FR) Analogues d'acrylates substitués de composés stéroïdes synthétiques, préparations pharmaceutiques contenant ces composés et procédés d'utilisation de ces composés pour inhiber la 5-$g(a)-réductase stéroïde, y compris pour réduire la taille de la prostate. On a également découvert des produits intermédiaires utilisés dans la production desdits composés.
• 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.