[2-[(8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] 3-[[3-[2-[(8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethoxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]disulfanyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate | 140209-97-8

• 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: [2-[(8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] 3-[[3-[2-[(8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethoxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]disulfanyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 140209-97-8
• 化学式: C₆₀H₈₂F₂N₂O₁₆S₂
• 分子量: 1189.44
• InChiKey: ZRQCDSVYQQIFLP-ZOUPTQIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  82
• 可旋转键数：
  21
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  329
• 氢给体数：
  6
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  [2-[(8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] 3-[[3-[2-[(8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethoxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]disulfanyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate 在 盐酸 作用下， 以 甲醇 为溶剂， 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 、 三乙胺 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 5.5h， 生成 [2-[(8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] 3-[[3-[2-[(8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethoxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]disulfanyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
  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