6,19-Epithiopregn-4-ene-3,20-dione | 405138-38-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻庚烷
• 英文名称: 6,19-Epithiopregn-4-ene-3,20-dione
• 英文别名: 6,19-Epithioprogesterone；(1S,2S,5S,6S,9S,10S,12R)-6-acetyl-5-methyl-19-thiapentacyclo[10.5.2.01,13.02,10.05,9]nonadec-13-en-15-one
• CAS: 405138-38-7
• 化学式: C₂₁H₂₈O₂S
• 分子量: 344.518
• InChiKey: TUHIBFNWRMDNOE-WEEZVYGMSA-N

物化性质

• 熔点：
  183-185 °C(Solvent: Ethyl acetate; Hexane)
• 沸点：
  517.3±50.0 °C(predicted)
• 密度：
  1.21±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  59.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6,19-Epithiopregn-4-ene-3,20-dione 在 oxone 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以45%的产率得到6,19-Epithiopregn-4-ene-3,20-dione S-oxide
  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：

  19-羟孕酮 在 吡啶 、 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 25.75h， 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

文献信息

• 6,19-Sulfur-Bridged Progesterone Analogues with Antiimmunosuppressive Activity
  作者：Adriana S. Veleiro、Adali Pecci、María C. Monteserín、Ricardo Baggio、María T. Garland、Carlos P. Lantos、Gerardo Burton

  DOI：10.1021/jm049266x

  日期：2005.9.1

  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.