3,3-ethylenedioxy-5α-hydroxy-11β-{4'-[1',1'-(ethylenedioxy)-2'2'2'-trifluoroethyl]phenyl}-estr-9-en-17-one | 1422259-26-4

• 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: 3,3-ethylenedioxy-5α-hydroxy-11β-{4'-[1',1'-(ethylenedioxy)-2'2'2'-trifluoroethyl]phenyl}-estr-9-en-17-one
• CAS: 1422259-26-4
• 化学式: C₃₀H₃₅F₃O₆
• 分子量: 548.6
• InChiKey: JFAQXQKODHJSLS-KDPBODAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.29
• 重原子数：
  39.0
• 可旋转键数：
  2.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  五氟碘乙烷 、 3,3-ethylenedioxy-5α-hydroxy-11β-{4'-[1',1'-(ethylenedioxy)-2'2'2'-trifluoroethyl]phenyl}-estr-9-en-17-one 在 methyllithium lithium bromide 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 2.0h， 以70%的产率得到17β-hydroxy-17α-pentafluoroethyl-11β-{4'-[1',1'-(ethylenedioxy)-2'2'2'-trifluoroethyl]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
• 作为产物：
  描述：

  3,3-ethylenedioxy-5α,10α-epoxy-17β-cyano-17α-trimethylsilyloxyestr-9(11)-ene 在 四丁基氟化铵 、 碘 、 magnesium 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 3,3-ethylenedioxy-5α-hydroxy-11β-{4'-[1',1'-(ethylenedioxy)-2'2'2'-trifluoroethyl]phenyl}-estr-9-en-17-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