(S)-2-{[(3S,3aS,5aS,6R,9aS,9bS)-6-(2-Carboxy-ethyl)-3a,6-dimethyl-7-oxo-dodecahydro-cyclopenta[a]naphthalene-3-carbonyl]-amino}-4-methyl-pentanoic acid ethyl ester | 180162-26-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-2-{[(3S,3aS,5aS,6R,9aS,9bS)-6-(2-Carboxy-ethyl)-3a,6-dimethyl-7-oxo-dodecahydro-cyclopenta[a]naphthalene-3-carbonyl]-amino}-4-methyl-pentanoic acid ethyl ester
• CAS: 180162-26-9
• 化学式: C₂₇H₄₃NO₆
• 分子量: 477.642
• InChiKey: BVHQGDBIMKJIHQ-NMADCLJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.37
• 重原子数：
  34.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  109.77
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-2-{[(3S,3aS,5aS,6R,9aS,9bS)-6-(2-Carboxy-ethyl)-3a,6-dimethyl-7-oxo-dodecahydro-cyclopenta[a]naphthalene-3-carbonyl]-amino}-4-methyl-pentanoic acid ethyl ester 在 platinum on activated charcoal 氢气 作用下， 以 乙二醇 为溶剂， 75.0~180.0 ℃ 、303.98 kPa 条件下， 反应 6.33h， 生成 (1S,3aS,3bS,5aR,9aR,9bS,11aS)-6,9a,11a-trimethyl-N-[(2S)-4-methyl-1-(methylamino)-1-oxopentan-2-yl]-7-oxo-2,3,3a,3b,4,5,5a,8,9,9b,10,11-dodecahydro-1H-indeno[5,4-f]quinoline-1-carboxamide
  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 、 potassium permanganate 、 sodium periodate 、 草酰氯 、 sodium carbonate 作用下， 以 水 、 甲苯 、 叔丁醇 为溶剂， 反应 6.75h， 生成 (S)-2-{[(3S,3aS,5aS,6R,9aS,9bS)-6-(2-Carboxy-ethyl)-3a,6-dimethyl-7-oxo-dodecahydro-cyclopenta[a]naphthalene-3-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