9Α-氟-21-碘-16Α-甲基孕甾-1,4-二烯-11Β,17Α-二醇-3,20-二酮 | 2029-18-7

• 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
• 中文名称: 9Α-氟-21-碘-16Α-甲基孕甾-1,4-二烯-11Β,17Α-二醇-3,20-二酮
• 中文别名: 9Α-氟-11Β,17Α-二羟基-21-碘-16Α-甲基孕甾-1,4-二烯-3,20-二酮
• 英文名称: 9-fluoro-11β,17-dihydroxy-21-iodo-16α-methylpregn-4-ene-3,20-dione
• 英文别名: dexamethasone-21-iodide；9-Fluoro-21-iodo-16-methylpregna-1,4-diene-11,17-diol-3,20-dion；(8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-17-(2-iodoacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
• CAS: 2029-18-7
• 化学式: C₂₂H₂₈FIO₄
• 分子量: 502.365
• InChiKey: KKOUPNKAJNZCGM-CXSFZGCWSA-N

物化性质

• 沸点：
  575.9±50.0 °C(Predicted)
• 密度：
  1.57±0.1 g/cm3(Predicted)
• 溶解度：
  二恶烷（轻微）、DMSO（轻微）、甲醇（轻微）

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  5

制备方法与用途

用途 

地塞米松磷酸钠的中间体。

反应信息

• 作为反应物：
  描述：

  9Α-氟-21-碘-16Α-甲基孕甾-1,4-二烯-11Β,17Α-二醇-3,20-二酮 在 盐酸 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 bis(2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl) 3,3'-disulfanediylbis(2-aminopropanoate)
  参考文献：
  名称：

  Synthesis of new local anti-inflammatory thiosteroids based on antedrug concept

  摘要：

  The synthesis and the in vitro pharmacological evaluation of a number of topical corticosteroid derivatives designed on the basis of the antedrug concept are reported. Three series of compounds were synthesized in which sulfur-containing amino acids were incorporated to the steroidal structure in the 21 position. Compounds of series I are diesters of cystine with the 21-hydroxyl groups of the corticosteroids, while series II and III contain 21-amino and 21-thio corticosteroid derivatives, respectively. The new compounds were less potent than the parent corticosteroids in vitro. The 21-yl-[9-alpha-fluoro-11-beta,17-alpha-dihydroxy-16-alpha-methyl-1,4-pregnadiene-3,20-dione]-S-acetylamino cysteine 13 was the most interesting compound of the series and is now under further evaluation.

  DOI：

  10.1016/0223-5234(91)90137-c
• 作为产物：
  描述：

  地塞米松 在 吡啶 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 3.5h， 生成 9Α-氟-21-碘-16Α-甲基孕甾-1,4-二烯-11Β,17Α-二醇-3,20-二酮
  参考文献：
  名称：

  Synthesis of new local anti-inflammatory thiosteroids based on antedrug concept

  摘要：

  The synthesis and the in vitro pharmacological evaluation of a number of topical corticosteroid derivatives designed on the basis of the antedrug concept are reported. Three series of compounds were synthesized in which sulfur-containing amino acids were incorporated to the steroidal structure in the 21 position. Compounds of series I are diesters of cystine with the 21-hydroxyl groups of the corticosteroids, while series II and III contain 21-amino and 21-thio corticosteroid derivatives, respectively. The new compounds were less potent than the parent corticosteroids in vitro. The 21-yl-[9-alpha-fluoro-11-beta,17-alpha-dihydroxy-16-alpha-methyl-1,4-pregnadiene-3,20-dione]-S-acetylamino cysteine 13 was the most interesting compound of the series and is now under further evaluation.

  DOI：

  10.1016/0223-5234(91)90137-c

文献信息

• Rapi, Gianfranco; Ginanneschi, Mauro; Chelli, Mario, Journal of Chemical Research, Miniprint, 1987, # 1, p. 101 - 109
  作者：Rapi, Gianfranco、Ginanneschi, Mauro、Chelli, Mario

  DOI：——

  日期：——