3β,5β,17β-三羟基-17α-(3-羟基-1-炔丙基<丙炔基>)-15β,16β-亚甲基-5β-雄甾-6-烯-17-酮 | 108674-97-1

• 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: 3β,5β,17β-三羟基-17α-(3-羟基-1-炔丙基<丙炔基>)-15β,16β-亚甲基-5β-雄甾-6-烯-17-酮
• 英文名称: 17α-(3-hydroxypropynyl)-15β,16β-methylene-5β-androst-6-ene-3β,5,17β-triol
• 英文别名: (1R,2S,3S,5S,6S,7S,10S,11R,14S,16R)-6-(3-Hydroxyprop-1-ynyl)-7,11-dimethylpentacyclo[8.8.0.02,7.03,5.011,16]octadec-17-ene-6,14,16-triol
• CAS: 108674-97-1
• 化学式: C₂₃H₃₂O₄
• 分子量: 372.505
• InChiKey: XOJNHZIWRNMDER-ZLWSQXOLSA-N

物化性质

• 沸点：
  557.9±50.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、二甲亚砜、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3β,5β,17β-三羟基-17α-(3-羟基-1-炔丙基<丙炔基>)-15β,16β-亚甲基-5β-雄甾-6-烯-17-酮 在 镍 吡啶 、 chromium(VI) oxide 、 水 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 70.0 ℃ 、101.33 kPa 条件下， 反应 18.0h， 生成 6,7-去亚甲基-6,7-去氢屈螺酮
  参考文献：
  名称：

  Aldosterone antagonists. 2. New 7.alpha.-(acetylthio)-15,16-methylene spirolactones

  摘要：

  Some 15,16-methylene derivatives of the aldosterone antagonist spironolactone were synthesized with the purpose of increasing the antialdosterone potency and reducing the endocrinological effects of this standard compound. By introduction of a 1,2-double bond and a 15 beta,16 beta-methylene ring in the spironolactone molecule both goals were achieved. In animal studies mespirenone exhibited a threefold-greater antialdosterone potency and less than 10% of the antiandrogenic activity of spironolactone.

  DOI：

  10.1021/jm00391a023
• 作为产物：
  描述：

  (3b,5b,15a,16a)-15,16-二氢-3,5-二羟基-3’H-环丙并[15,16]雄甾-6,15-二烯-17-酮 、 2-丙炔-1-醇 在 potassium ethoxide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以82.5%的产率得到3β,5β,17β-三羟基-17α-(3-羟基-1-炔丙基<丙炔基>)-15β,16β-亚甲基-5β-雄甾-6-烯-17-酮
  参考文献：
  名称：

  Aldosterone antagonists. 2. New 7.alpha.-(acetylthio)-15,16-methylene spirolactones

  摘要：

  Some 15,16-methylene derivatives of the aldosterone antagonist spironolactone were synthesized with the purpose of increasing the antialdosterone potency and reducing the endocrinological effects of this standard compound. By introduction of a 1,2-double bond and a 15 beta,16 beta-methylene ring in the spironolactone molecule both goals were achieved. In animal studies mespirenone exhibited a threefold-greater antialdosterone potency and less than 10% of the antiandrogenic activity of spironolactone.

  DOI：

  10.1021/jm00391a023

文献信息

• NICKISCH, K.;BITTLER, D.;LAURENT, H.;LOSERT, W.;CASALS-STENZEL, J.;NISHIN+, J. MED. CHEM., 30,(1987) N 8, 1403-1409
  作者：NICKISCH, K.、BITTLER, D.、LAURENT, H.、LOSERT, W.、CASALS-STENZEL, J.、NISHIN+

  DOI：——

  日期：——
• Aldosterone antagonists. 2. New 7.alpha.-(acetylthio)-15,16-methylene spirolactones
  作者：Klaus Nickisch、Dieter Bittler、Henry Laurent、Wolfgang Losert、Jorge Casals-Stenzel、Yukishige Nishino、Ekkehard Schillinger、Rudolf Wiechert

  DOI：10.1021/jm00391a023

  日期：1987.8

  Some 15,16-methylene derivatives of the aldosterone antagonist spironolactone were synthesized with the purpose of increasing the antialdosterone potency and reducing the endocrinological effects of this standard compound. By introduction of a 1,2-double bond and a 15 beta,16 beta-methylene ring in the spironolactone molecule both goals were achieved. In animal studies mespirenone exhibited a threefold-greater antialdosterone potency and less than 10% of the antiandrogenic activity of spironolactone.