(S)-2-[((8S,9S,10R,13S,14S,17S)-10,13-Dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carbonyl)-amino]-4-methyl-pentanoic acid ethyl ester | 180162-25-8

• 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: (S)-2-[((8S,9S,10R,13S,14S,17S)-10,13-Dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carbonyl)-amino]-4-methyl-pentanoic acid ethyl ester
• CAS: 180162-25-8
• 化学式: C₂₈H₄₃NO₄
• 分子量: 457.654
• InChiKey: TVQZAENROCICKU-LJAPERKMSA-N

物化性质

• 沸点：
  597.5±50.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.23
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  72.47
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-2-[((8S,9S,10R,13S,14S,17S)-10,13-Dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carbonyl)-amino]-4-methyl-pentanoic acid ethyl ester 在 potassium permanganate 、 sodium periodate 、 sodium carbonate 作用下， 以 水 、 乙二醇 、 叔丁醇 为溶剂， 反应 2.08h， 生成 (4aR,4bS,6aS,7S,9aS,9bS)-1,4a,6a-Trimethyl-2-oxo-2,3,4,4a,4b,5,6,6a,7,8,9,9a,9b,10-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxylic acid ((S)-3-methyl-1-methylcarbamoyl-butyl)-amide
  参考文献：
  名称：

  Substrate interaction with 5α-reductase enzyme: influence of the 17β-chain chirality in the mechanism of action of 4-azasteroid inhibitors

  摘要：

  A series of steroidal compounds were synthesized in order to evaluate the possible influence of the configuration of a stereocenter in the 17 beta -side chain on the inhibitory activity on the enzyme 5 alpha -reductase (5AR). For this purpose diastereomerically pure 4-azasteroids epimers at C-22 were prepared (compounds 1-11) and tested as inhibitors of 5AR in 'in vitro' tests, The obtained data showed that in most cases the couples of epimers possess a significant difference in their biological activity. We also considered, for the tested molecules, a series of chemico-physical parameters in order to find a possible correlation with their biological activity. The findings allowed us to propose a model of the binding site of 5AR which comprises also, for 4-azasteroid inhibitors, the configurational aspect of the 17 beta -side chain. (C) 2001 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(01)00114-3
• 作为产物：
  描述：

  3-氧代-雄甾-4-烯-17beta-羧酸 在 吡啶 、 草酰氯 作用下， 以 甲苯 为溶剂， 反应 5.0h， 生成 (S)-2-[((8S,9S,10R,13S,14S,17S)-10,13-Dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carbonyl)-amino]-4-methyl-pentanoic acid ethyl ester
  参考文献：
  名称：

  Substrate interaction with 5α-reductase enzyme: influence of the 17β-chain chirality in the mechanism of action of 4-azasteroid inhibitors

  摘要：

  A series of steroidal compounds were synthesized in order to evaluate the possible influence of the configuration of a stereocenter in the 17 beta -side chain on the inhibitory activity on the enzyme 5 alpha -reductase (5AR). For this purpose diastereomerically pure 4-azasteroids epimers at C-22 were prepared (compounds 1-11) and tested as inhibitors of 5AR in 'in vitro' tests, The obtained data showed that in most cases the couples of epimers possess a significant difference in their biological activity. We also considered, for the tested molecules, a series of chemico-physical parameters in order to find a possible correlation with their biological activity. The findings allowed us to propose a model of the binding site of 5AR which comprises also, for 4-azasteroid inhibitors, the configurational aspect of the 17 beta -side chain. (C) 2001 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(01)00114-3