Trifluoro-methanesulfonic acid (8S,9S,10S,13S,14S,17S)-17-acetyl-13-methyl-3-oxo-1,2,3,6,7,8,9,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-10-ylmethyl ester | 405138-46-7

• 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: Trifluoro-methanesulfonic acid (8S,9S,10S,13S,14S,17S)-17-acetyl-13-methyl-3-oxo-1,2,3,6,7,8,9,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-10-ylmethyl ester
• 英文别名: [(8S,9S,10S,13S,14S,17S)-17-acetyl-13-methyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-10-yl]methyl trifluoromethanesulfonate
• CAS: 405138-46-7
• 化学式: C₂₂H₂₉F₃O₅S
• 分子量: 462.53
• InChiKey: RQNNSPGHYYRCBQ-NXMWLWCLSA-N

物化性质

• 沸点：
  528.0±50.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  85.9
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Trifluoro-methanesulfonic acid (8S,9S,10S,13S,14S,17S)-17-acetyl-13-methyl-3-oxo-1,2,3,6,7,8,9,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-10-ylmethyl ester 在 氢氧化钾 、 碘 、 对甲苯磺酸 、 三乙胺 、 原甲酸三乙酯 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 24.75h， 生成 6,19-Epithiopregn-4-ene-3,20-dione
  参考文献：
  名称：

  6,19-Sulfur-Bridged Progesterone Analogues with Antiimmunosuppressive Activity

  摘要：

  Sulfur-bridged pregnanes 6,19-epithioprogesterone, 21-hydroxy-6,19-epithioprogesterone, and the corresponding sulfoxides and sulfones were synthesized and tested as blockers of the immunosuppresive activity of dexamethasone in rat thymocytes. A new one-pot procedure is described for the preparation of 6,19-epithioprogesterone and related compounds by iodocyclization of a 19-sulfanylpregn-5-ene. Antiimmunosuppresive activity was evaluated by the ability of the different steroids to block dexamethasone-inediated apoptosis in thymocytes and dexamethasone-mediated inhibition of the NF kappa-B transcription factor activity. DNA fragmentation and annexin V-FITC positive cells were taken as parameters of apoptosis whereas NF kappa-B activity was tested by the expression of the reporter vector kappa B-luciferase by TNF-alpha in Hela cells. 21-Hydroxy-6,19-epithioprogesterone S,S-dioxide-had improved activity in both parameters, while 21-hydroxy-6,19-epithioprogesterone had improved activity only in blocking dexamethasone-induced programmed cell death.

  DOI：

  10.1021/jm049266x
• 作为产物：
  描述：

  三氟甲磺酸酐 、 19-羟孕酮 在 吡啶 作用下， 反应 1.0h， 生成 Trifluoro-methanesulfonic acid (8S,9S,10S,13S,14S,17S)-17-acetyl-13-methyl-3-oxo-1,2,3,6,7,8,9,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-10-ylmethyl ester
  参考文献：
  名称：

  6,19-Sulfur-Bridged Progesterone Analogues with Antiimmunosuppressive Activity

  摘要：

  Sulfur-bridged pregnanes 6,19-epithioprogesterone, 21-hydroxy-6,19-epithioprogesterone, and the corresponding sulfoxides and sulfones were synthesized and tested as blockers of the immunosuppresive activity of dexamethasone in rat thymocytes. A new one-pot procedure is described for the preparation of 6,19-epithioprogesterone and related compounds by iodocyclization of a 19-sulfanylpregn-5-ene. Antiimmunosuppresive activity was evaluated by the ability of the different steroids to block dexamethasone-inediated apoptosis in thymocytes and dexamethasone-mediated inhibition of the NF kappa-B transcription factor activity. DNA fragmentation and annexin V-FITC positive cells were taken as parameters of apoptosis whereas NF kappa-B activity was tested by the expression of the reporter vector kappa B-luciferase by TNF-alpha in Hela cells. 21-Hydroxy-6,19-epithioprogesterone S,S-dioxide-had improved activity in both parameters, while 21-hydroxy-6,19-epithioprogesterone had improved activity only in blocking dexamethasone-induced programmed cell death.

  DOI：

  10.1021/jm049266x