15α,16α-methylene-3-oxo-17α-pregna-4,6-diene-21,17-carbolactone | 67372-64-9

• 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: 15α,16α-methylene-3-oxo-17α-pregna-4,6-diene-21,17-carbolactone
• 英文别名: (1'R,2'S,3'R,5S,5'R,7'S,10'S,11'R)-7',11'-dimethylspiro[oxolane-5,6'-pentacyclo[8.8.0.02,7.03,5.011,16]octadeca-15,17-diene]-2,14'-dione
• CAS: 67372-64-9
• 化学式: C₂₃H₂₈O₃
• 分子量: 352.474
• InChiKey: OMQDQOBQNOHRKO-PWMNKVPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  26.0
• 可旋转键数：
  0.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  15α,16α-methylene-3-oxo-17α-pregna-4,6-diene-21,17-carbolactone 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以70%的产率得到15α,16α-methylene-3-oxo-17α-pregna-1,4,6-triene-21,17-carbolactone
  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：

  (4aR,4bS,6aS,7S,7aR,8aR,8bR,8cR)-2-ethoxy-4a,6a-dimethyl-3',4,4a,4b,4',5,6,6a,7a,8,8a,8b,8c,9-tetradecahydro-3H,5'H-spiro[cyclopropa[4,5]cyclopenta[1,2-a]phenanthrene-7,2'-furan]-5'-one 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 水 、 sodium acetate 、 lithium carbonate 、 lithium bromide 作用下， 生成 15α,16α-methylene-3-oxo-17α-pregna-4,6-diene-21,17-carbolactone
  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

• Aldosterone antagonists. 3. Synthesis and activities of steroidal 7.alpha.-(alkoxycarbonyl)-15,16-methylene spirolactones
  作者：Klaus Nickisch、Dieter Bittler、Henry Laurent、Wolfgang Losert、Yukishige Nishino、Ekkehard Schillinger、Rudolf Wiechert

  DOI：10.1021/jm00164a007

  日期：1990.2

  Several A- and D-ring substituted steroidal 7 alpha-alkoxycarbonyl spirolactones were synthesized with the purpose of increasing the aldosterone antagonistic potency and reducing the endocrinological side effects relative to the standard drug spironolactone. It was found that the 15 beta,16 beta-methylene derivative 17 exhibited a 2-fold higher aldosterone antagonistic activity compared to either spironolactone

  相对于标准药物螺内酯，合成了几种A和D环取代的甾体7α-烷氧基羰基螺内酯，目的是增加醛固酮的拮抗力并减少内分泌副作用。已经发现，与螺内酯或15，16-未取代的衍生物29相比，15β，16β-亚甲基衍生物17表现出高两倍的醛固酮拮抗活性，同时显示出显着降低的抗雄激素性。
• NICKISCH, K.;LAURENT, H.
  作者：NICKISCH, K.、LAURENT, H.

  DOI：——

  日期：——
• 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：——