3,3-ethylenedioxy-5a,17β-dihydroxy-17-(3,3,3-trifluoroprop-1(E)-enyl)-11β-{4'-[1',1'-(ethylenedioxy)-ethyl]phenyl}-estr-9-ene | 1421036-60-3

• 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-5a,17β-dihydroxy-17-(3,3,3-trifluoroprop-1(E)-enyl)-11β-{4'-[1',1'-(ethylenedioxy)-ethyl]phenyl}-estr-9-ene
• 英文别名: (E)-3,3-ethylenedioxy-5α,17β-dihydroxy-17-(3,3,3-trifluoroprop-1-enyl)-11'-{4'-[1',1'-(ethylenedioxy)ethyl]phenyl}estr-9-ene；(5'R,8'S,11'R,13'S,14'S,17'R)-13'-methyl-11'-[4-(2-methyl-1,3-dioxolan-2-yl)phenyl]-17'-[(E)-3,3,3-trifluoroprop-1-enyl]spiro[1,3-dioxolane-2,3'-2,4,6,7,8,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene]-5',17'-diol
• CAS: 1421036-60-3
• 化学式: C₃₃H₄₁F₃O₆
• 分子量: 590.68
• InChiKey: OFQZTXFMIODTNY-AKOWLWKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  42
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3,3-ethylenedioxy-5a,17β-dihydroxy-17-(3,3,3-trifluoroprop-1(E)-enyl)-11β-{4'-[1',1'-(ethylenedioxy)-ethyl]phenyl}-estr-9-ene 在 硫酸 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以700 mg的产率得到11β-(4'-acetylphenyl)-17β-hydroxy-17-(3,3,3-trifluoroprop-1(E)-enyl)-estra-4,9-diene-3-one
  参考文献：
  名称：

  Synthesis and antiprogestational properties of novel 17-fluorinated steroids

  摘要：

  Progesterone receptor (PR) plays a key role in reproductive functions, and compounds that inhibit progesterone action (antiprogestins) have potential use in the treatment of estrogen- and progesterone-dependent diseases, including uterine leiomyomas and breast cancer. In the present study, we chemically synthesized novel 17-fluorinated steroids and evaluated the cytotoxicity profiles of these compounds in T47D breast cancer cells compared to the activity of known antiprogestins, including ZK230 211, RU-486, CDB2914, CDB4124 and ORG33628. We analyzed in vitro receptor-binding assays and PR-transactivation assays to establish the antiprogestational activity of these molecules. The representative anti-progestin EC304 was found to inhibit in vitro tumorigenicity in a dose-dependent fashion in T47D cells by a colony formation assay at 1 and 10 nM concentrations. The potent in vivo antiprogestational activity of EC304 was also demonstrated in an antinidation assay for the interruption of early pregnancy in rats. The strong antiprogestational activity and absence of antiglucocorticoid activity in EC compounds may demonstrate their utility in the treatment of leiomyoma, endometriosis and breast cancer. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2013.04.003
• 作为产物：
  描述：

  3,3-ethylenedioxy-5α,17β-dihydroxy-17-(3,3,3-trifluoro-1-propynyl)-11β-{4'-[1',1'-(ethylenedioxy)-ethyl]phenyl}-estr-9-ene 在 红铝 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 4.0h， 生成 3,3-ethylenedioxy-5a,17β-dihydroxy-17-(3,3,3-trifluoroprop-1(E)-enyl)-11β-{4'-[1',1'-(ethylenedioxy)-ethyl]phenyl}-estr-9-ene
  参考文献：
  名称：

  [EN] PROGESTERONE ANTAGONISTS
  [FR] ANTAGONISTES DE PROGESTÉRONE

  摘要：

  本文描述了一些化合物，它们要么作为纯抗孕激素，要么作为具有部分激动活性的抗孕激素，并且使用这些化合物治疗癌症的方法。

  公开号：

  WO2013016725A1

文献信息

• PROGESTERONE ANTAGONISTS
  申请人：Nickisch Klaus

  公开号：US20130029953A1

  公开（公告）日：2013-01-31

  Described herein are compounds which either act as pure antiprogestins or as antiprogestins with partial agonistic activity and methods of treating cancer using such compounds.

  本文描述了一些化合物，它们可以作为纯抗孕激素或具有部分激动活性的抗孕激素，并且使用这些化合物的方法治疗癌症。