17β-hydroxy-17α-(1,1,2,2,2-pentafluoroethyl)-11β-[4'-(2'2'2'-trifluoracetyl)phenyl]-estra-4,9-dien-3-one | 1422447-21-9

• 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: 17β-hydroxy-17α-(1,1,2,2,2-pentafluoroethyl)-11β-[4'-(2'2'2'-trifluoracetyl)phenyl]-estra-4,9-dien-3-one
• 英文别名: EC316；(8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-17-(1,1,2,2,2-pentafluoroethyl)-11-[4-(2,2,2-trifluoroacetyl)phenyl]-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one
• CAS: 1422447-21-9
• 化学式: C₂₈H₂₆F₈O₃
• 分子量: 562.5
• InChiKey: KOTHQQTWTKAARH-KOSDUOMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  39
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  3,3-ethylenedioxy-5α,17β-dihydroxy-17-(1,1,2,2,2-pentafluoroethyl)-11β-[4'-(tert-butyldimethylsilyloxymethyl)phenyl]-estr-9-ene 在 四丙基高钌酸铵 、 四丁基氟化铵 、 三氧化硫吡啶 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 4.0h， 生成 17β-hydroxy-17α-(1,1,2,2,2-pentafluoroethyl)-11β-[4'-(2'2'2'-trifluoracetyl)phenyl]-estra-4,9-dien-3-one
  参考文献：
  名称：

  Synthesis and biological evaluation of partially fluorinated antiprogestins and mesoprogestins

  摘要：

  A series of antiprogestins have been synthesized by partially fluorinating the steroid molecule in positions relevant for receptor binding. By introducing fluorine at the exo-methylene of the 17 spirofuran ring, we obtained partial agonists (mesoprogestins) with significant applications for antiproliferative and antiovulatory treatment strategies in gynecological therapy such as uterine fibroids, endometriosis and heavy menstrual bleeding. Compared to the standard drug RU486, our synthesized compounds exhibited considerable dissociation between antiprogestational and antiglucocorticoid PR receptors. Furthermore, our studies have shown that pure antiprogestins can be generated by partially fluorinating the 17 propenyl and propynl group or by substituting the 4' acetyl phenyl group in the 11 position using trifluromethyl group. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.09.010