2',2',2'-Trifluoromethoxyestradiol | 192062-07-0

• 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',2',2'-Trifluoromethoxyestradiol
• 英文别名: 2-(2',2',2'-Trifluoroethoxy)estra-1,3,5(10)-Trien-3,17β-Diol；2-(2',2',2'-trifluoroethoxy)estradiol；2-(2,2,2-Trifluoroethoxy)estradiol；(8R,9S,13S,14S,17S)-13-methyl-2-(2,2,2-trifluoroethoxy)-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
• CAS: 192062-07-0
• 化学式: C₂₀H₂₅F₃O₃
• 分子量: 370.412
• InChiKey: SEJLRFOCUWYOPK-SSTWWWIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2',2',2'-Trifluoromethoxyestradiol 在 吡啶 、 chromium(VI) oxide 、 溶剂黄146 作用下， 反应 2.0h， 生成 3,17β-bis(acetyloxy)-2-(2',2',2'-trifluoroethoxy)-6-estra-1,3,5(10)-triene
  参考文献：
  名称：

  Synthesis of Analogs of 2-Methoxyestradiol with Enhanced Inhibitory Effects on Tubulin Polymerization and Cancer Cell Growth

  摘要：

  A new series of estradiol analogs was synthesized in an attempt to improve on the anticancer activity of 2-methoxyestradiol, a naturally occurring mammalian tubulin polymerization inhibitor. The compounds were evaluated as inhibitors of tubulin polymerization and the binding of [H-3]colchicine to tubulin, as well as for in vitro cytotoxicity in human cancer cell cultures. Overall, the most potent of the new compounds were 2-(2',2',2'-trifluoroethoxy)-6-oximinoestradiol, 2-ethoxy-6-oximinoestradiol, and 2-ethoxy-6-methoximinoestradiol. These agents lacked significant affinity for the estrogen receptor. The cytotoxicities of the compounds correlated in general with their abilities to inhibit tubulin polymerization, thus supporting inhibition of tubulin polymerization as the primary mechanism causing inhibition of cell growth.

  DOI：

  10.1021/jm9700833
• 作为产物：
  描述：

  3,17β-bis(benzyloxy)estra-1,3,5(10)-triene 在 palladium dihydroxide 正丁基锂 、 硫酸 、 氢气 、 溴 、 potassium carbonate 、 对甲苯磺酸 、 溶剂黄146 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， -78.0~130.0 ℃ 、344.73 kPa 条件下， 反应 49.5h， 生成 2',2',2'-Trifluoromethoxyestradiol
  参考文献：
  名称：

  Synthesis of Analogs of 2-Methoxyestradiol with Enhanced Inhibitory Effects on Tubulin Polymerization and Cancer Cell Growth

  摘要：

  A new series of estradiol analogs was synthesized in an attempt to improve on the anticancer activity of 2-methoxyestradiol, a naturally occurring mammalian tubulin polymerization inhibitor. The compounds were evaluated as inhibitors of tubulin polymerization and the binding of [H-3]colchicine to tubulin, as well as for in vitro cytotoxicity in human cancer cell cultures. Overall, the most potent of the new compounds were 2-(2',2',2'-trifluoroethoxy)-6-oximinoestradiol, 2-ethoxy-6-oximinoestradiol, and 2-ethoxy-6-methoximinoestradiol. These agents lacked significant affinity for the estrogen receptor. The cytotoxicities of the compounds correlated in general with their abilities to inhibit tubulin polymerization, thus supporting inhibition of tubulin polymerization as the primary mechanism causing inhibition of cell growth.

  DOI：

  10.1021/jm9700833

文献信息

• [EN] METHOD AND INTERMEDIATES FOR PREPARING 2-ALKOXY AND 2-ARYLOXY ESTROGEN COMPOUNDS<br/>[FR] PROCÉDÉ ET INTERMÉDIAIRES POUR LA PRÉPARATION DE COMPOSÉS 2-ALCOXY ET 2-ARYLOXY OETROGÈNE
  申请人：NAXOSPHARMA S R L

  公开号：WO2010043506A1

  公开（公告）日：2010-04-22

  Method for preparing 2-alkoxy and 2-aryloxyestrogen compounds, and the intermediate compounds prepared during the use of this method, which intermediate compounds are useful intermediates in the preparation of certain physiologically active compounds.

  制备2-烷氧基和2-芳氧基雌激素化合物的方法，以及在使用该方法期间制备的中间化合物，这些中间化合物是在制备某些生理活性化合物时有用的中间体。
• Synthesis of 2-alkoxyestradiols
  申请人：Pharm-Eco Laboratories, Inc.

  公开号：US06051726A1

  公开（公告）日：2000-04-18

  Disclosed is a method of preparing a compound represented by the following structural formula: ##STR1## The method comprises reacting bromine (Br.sub.2) and an aliphatic organic acid with a compound represented by the following structural formula: ##STR2## R.sub.1 and R.sub.2 are each independently a hydroxyl protecting group.

  本发明揭示了一种制备下列结构式所代表的化合物的方法：##STR1## 该方法包括将溴（Br.sub.2）和脂肪族有机酸与下列结构式所代表的化合物反应：##STR2## 其中R.sub.1和R.sub.2各自独立地是羟基保护基。
• SYNTHESIS OF 2-ALKOXYESTRADIOLS
  申请人：Pharm-Eco Laboratoires, Incorporated

  公开号：EP0984979A1

  公开（公告）日：2000-03-15
• METHOD AND INTERMEDIATES FOR PREPARING 2-ALKOXY AND 2-ARYLOXY ESTROGEN COMPOUNDS
  申请人：Naxospharma S.R.L.

  公开号：EP2344515A1

  公开（公告）日：2011-07-20
• Method and intermediates for preparing 2-alkoxy and 2-aryloxy estrogen compounds
  申请人：Lombardi Paolo

  公开号：US20100099141A1

  公开（公告）日：2010-04-22

  The present invention relates to a method for preparing 2-alkoxy and 2-aryloxyestrogen compounds, and the intermediate compounds prepared during the use of this method, which intermediate compounds are useful intermediates in the preparation of certain physiologically active compounds.