15α,16α-methylene-3-oxo-17α-pregna-4-ene-21,17-carbolactone | 67372-62-7

• 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-ene-21,17-carbolactone
• 英文别名: (1'R,2'R,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]octadec-15-ene]-2,14'-dione
• CAS: 67372-62-7
• 化学式: C₂₃H₃₀O₃
• 分子量: 354.489
• InChiKey: DYIJDDWIJGVQBE-PWMNKVPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.45
• 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：
  0.83
• 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-ene-21,17-carbolactone 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 硫酸 、 水 、 sodium acetate 、 lithium carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 lithium bromide 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 甲苯 为溶剂， 反应 44.5h， 生成 Δ¹-15α,16α-methylene-spironolactone
  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：

  (1R,2R,3R,5R,7S,10S,11R,14S)-14-hydroxy-7,11-dimethylpentacyclo[8.8.0.02,7.03,5.011,16]octadec-16-en-6-one 在 Lindlar's catalyst potassium ethoxide 、 氢气 、 环己酮 、 aluminum isopropoxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 13.5h， 生成 15α,16α-methylene-3-oxo-17α-pregna-4-ene-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. 4. Synthesis and activities of steroidal 6,6-ethylene-15,16-methylene 17-spirolactones
  作者：Klaus Nickisch、Sybille Beier、Dieter Bittler、Walter Elger、Henry Laurent、Wolfgang Losert、Yukishige Nishino、Ekkehard Schillinger、Rudolf Wiechert

  DOI：10.1021/jm00112a022

  日期：1991.8

  Several steroidal 6,6-ethylene-15,16-methylene 17-spirolactones were synthesized to find new progestogens that exhibit both progestational and antimineralocorticoidal activities. The influence of substituents in the 10- and 13-position of the steroidal framework on both properties was investigated. It was found that only compound 12, carrying methyl groups at the 10- and 13-positions, possesses high

  合成了几种甾体6,6-乙烯-15,16-亚甲基17-螺内酯，以发现具有孕激素和抗盐皮质激素活性的新孕激素。研究了甾族骨架的10位和13位取代基对两种性质的影响。已经发现只有在10和13位带有甲基的化合物12具有高的孕激素和抗盐皮质激素活性。
• NICKISCH, KLAUS;BEIER, SYBILLE;BITTLER, DIETER;ELGER, WALTER;LAURENT, HEN+, J. MED. CHEM., 34,(1991) N, C. 2464-2468
  作者：NICKISCH, KLAUS、BEIER, SYBILLE、BITTLER, DIETER、ELGER, WALTER、LAURENT, HEN+

  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：——