(13S,17S)-17-hydroxy-2-methoxy-13-methyl-7,8,9,11,12,13,14,15, 16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl trifluoromethanesulfonate | 824946-75-0

• 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: (13S,17S)-17-hydroxy-2-methoxy-13-methyl-7,8,9,11,12,13,14,15, 16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl trifluoromethanesulfonate
• 英文别名: 3-triflate-2-methoxyestra-1,3,5(10)-trien-17β-ol；[(8R,9S,13S,14S,17S)-17-hydroxy-2-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] trifluoromethanesulfonate
• CAS: 824946-75-0
• 化学式: C₂₀H₂₅F₃O₅S
• 分子量: 434.477
• InChiKey: HEIXVPWXEKAWEG-SSTWWWIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  81.2
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (13S,17S)-17-hydroxy-2-methoxy-13-methyl-7,8,9,11,12,13,14,15, 16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl trifluoromethanesulfonate 、 三丁基乙烯基锡 在 bis-triphenylphosphine-palladium(II) chloride 2,6-二叔丁基-4-甲基苯酚 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 、 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 40.0h， 以60%的产率得到2-methoxy-3-(vinyl)estra-1,3,5(10)-triene-17β-ol
  参考文献：
  名称：

  Antiangiogenic agents

  摘要：

  通过给予一般公式中的化合物治疗具有不良血管生成特征的哺乳动物疾病的方法和组合物。其中，变量在规范中有定义。

  公开号：

  US20050014737A1
• 作为产物：
  描述：

  4-硝基苯酚三氟甲基磺酸酯 、 2-甲氧基雌二醇 生成 (13S,17S)-17-hydroxy-2-methoxy-13-methyl-7,8,9,11,12,13,14,15, 16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl trifluoromethanesulfonate
  参考文献：
  名称：

  Antiangiogenic agents

  摘要：

  通过向哺乳动物疾病或状况中施用上述公式化合物的有效量来治疗其特征为不良血管生成的组合物和治疗方法： 其中 R a 从—OCH 3 ，—OCH 2 CH 3 或—CCCH 3 中选择；Z从>C(H)—OH，>C(H)—O-烷基，>C(H)—O-磺酸酯中选择，其中烷基是由1至10个碳组成的线性、支链和/或环烃链。

  公开号：

  US20050203075A1

文献信息

• Synthesis and antitumor activities of 3-modified 2-methoxyestradiol analogs
  作者：Lita S. Suwandi、Gregory E. Agoston、Jamshed H. Shah、Arthur D. Hanson、Xiaoguo H. Zhan、Theresa M. LaVallee、Anthony M. Treston

  DOI：10.1016/j.bmcl.2009.09.009

  日期：2009.11

  The syntheses of 2-methoxyestradiol analogs with modifications at the 3-position are described. The analogs were assessed for their antiproliferative, antiangiogenic, and estrogenic activities. Several lead substituents were identified with similar or improved antitumor activities and reduced metabolic liability compared to 2-methoxyestradiol. (C) 2009 Elsevier Ltd. All rights reserved.
• Structure elucidation by synthesis of four metabolites of the antitumor drug ENMD-1198 detected in human plasma samples
  作者：Zhenglai Fang、Gregory E. Agoston、Gaetan Ladouceur、Anthony M. Treston、LiQuan Wang、Mark Cushman

  DOI：10.1016/j.tet.2009.10.046

  日期：2009.12

  ENMD-1198 is a biologically active analogue of the antitumor drug 2-methoxyestradiol. Four human metabolites of ENMD-1198 were identified through synthesis and liquid chromatography/mass spectrometry comparisons of the metabolites with the synthetic standards. Two metabolites (3 and 4) are epimers resulting from benzylic hydroxylation at C-6. Two additional metabolites (5 and 6) are formed by epimeric hydroxylation at C-6 and alpha-epoxidation of the 16,17-alkene. The syntheses provided sufficient quantities of the metabolites for cytotoxicity studies to proceed. The 6-beta-ol 4 was moderately less cytotoxic than the parent drug, while the remaining three metabolites (3, 5, and 6) were significantly less cytotoxic. (C) 2009 Elsevier Ltd. All rights reserved.
• Antiangiogenic agents
  申请人：Agoston E. Gregory

  公开号：US20050203075A1

  公开（公告）日：2005-09-15

  Compositions and methods for treating mammalian diseases or conditions characterized by undesirable angiogenesis by administering an effective amount of a compound of the formulae: wherein R a is selected from —OCH 3 , —OCH 2 CH 3 or —CCCH 3 ; and Z is selected from >C(H)—OH, >C(H)—O-alkyl, >C(H)—O-sulfamate, where alkyl is a linear, branched and/or cyclic hydrocarbon chain comprising 1 to 10 carbons.

  通过向哺乳动物疾病或状况中施用上述公式化合物的有效量来治疗其特征为不良血管生成的组合物和治疗方法： 其中 R a 从—OCH 3 ，—OCH 2 CH 3 或—CCCH 3 中选择；Z从>C(H)—OH，>C(H)—O-烷基，>C(H)—O-磺酸酯中选择，其中烷基是由1至10个碳组成的线性、支链和/或环烃链。