17-oxo-19-norandrosta-3,5-dien-3-oic acid | 1393748-71-4

• 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: 17-oxo-19-norandrosta-3,5-dien-3-oic acid
• 英文别名: (8R,9S,10R,13S,14S)-13-methyl-17-oxo-2,7,8,9,10,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3-carboxylic acid
• CAS: 1393748-71-4
• 化学式: C₁₉H₂₄O₃
• 分子量: 300.398
• InChiKey: FCFPLTRQOYJAKG-RGQDEETRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  19-去甲-4-雄烯二酮 在 三溴化磷 、 溶剂黄146 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 53.0h， 生成 17-oxo-19-norandrosta-3,5-dien-3-oic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of novel unsaturated carboxysteroids as human 5α-reductase inhibitors: A legitimate approach

  摘要：

  In the present study, novel steroidal 17a-substituted 3-cyano-17a-aza-D-homo-3,5-androstadien-17-ones (12-19) and 17a-substituted 17-oxo-17a-aza-D-homo-3,5-androstadien-3-oic acids (20-26) were synthesized from dehydroepiandrosterone acetate (6) along with 17-oxo-19-nor-3,5-androstadien-3-oic acid (30) through a multistep synthesis. Compounds were evaluated for their in vitro 5 alpha-reductase inhibitory activity by measuring the conversion of PHI androstenedione in human embryonic kidney (HEK) cells. In vivo 5 alpha-reductase inhibitory activity was also determined using rat prostate weighing method. Compounds 21-23 and 25 showed potent inhibition of 5a-reductase II enzyme with IC50 values of 54.1 +/- 9.5, 22.1 +/- 2.4, 72.8 +/- 2.3 and 26.5 +/- 4.4 nM respectively as compared to Finasteride (30.3 nM) along with a significant (p < 0.05) reduction in rat prostate weight. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.026