9β,11β-epoxy-17α-[(3-ethyl-2-furanylcarbonyl)oxy]-6α-fluoro-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxylic acid methyl ester | 785806-98-6

• 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: 9β,11β-epoxy-17α-[(3-ethyl-2-furanylcarbonyl)oxy]-6α-fluoro-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxylic acid methyl ester
• CAS: 785806-98-6
• 化学式: C₂₉H₃₃FO₇
• 分子量: 512.575
• InChiKey: NJLLNGANCZSDCR-YDAYUMEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  37.0
• 可旋转键数：
  4.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  95.34
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  9β,11β-epoxy-17α-[(3-ethyl-2-furanylcarbonyl)oxy]-6α-fluoro-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxylic acid methyl ester 在 盐酸 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以34%的产率得到9α-chloro-6α-fluoro-17α-[(3-ethyl-2-furanylcarbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and biological properties of novel glucocorticoid androstene C-17 furoate esters

  摘要：

  A series of novel corticosteroid derivatives featuring C-17 furoate ester functionality have been synthesised. Profiling in vitro and in vivo has resulted in the identification of a compound with a longer duration of action and a lower oral side effect profile in rodents compared to budesonide. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.06.027
• 作为产物：
  描述：

  (6α,9β,11β,16α,17α)-9,11-epoxy-6-fluoro-17-hydroxy-16-methyl-3-oxo-androsta-1,4-diene-17-carboxylic acid 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 9β,11β-epoxy-17α-[(3-ethyl-2-furanylcarbonyl)oxy]-6α-fluoro-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and biological properties of novel glucocorticoid androstene C-17 furoate esters

  摘要：

  A series of novel corticosteroid derivatives featuring C-17 furoate ester functionality have been synthesised. Profiling in vitro and in vivo has resulted in the identification of a compound with a longer duration of action and a lower oral side effect profile in rodents compared to budesonide. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.06.027