(13S,17S)-2-methoxy-13-methyl-6-oxo-3-(trifluoromethylsulfonyloxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl acetate | 1204770-26-2

• 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)-2-methoxy-13-methyl-6-oxo-3-(trifluoromethylsulfonyloxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl acetate
• CAS: 1204770-26-2
• 化学式: C₂₂H₂₅F₃O₇S
• 分子量: 490.498
• InChiKey: FQHILHHDRVXFKE-XWHLSNAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.35
• 重原子数：
  33.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  95.97
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (13S,17S)-2-methoxy-13-methyl-6-oxo-3-(trifluoromethylsulfonyloxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl acetate 在 硼烷四氢呋喃络合物 、 (S)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.0h， 生成 (6S,13S,17S)-6-hydroxy-2-methoxy-13-methyl-3-(trifluoromethylsulfonyloxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl acetate 、 (6R,13S,17S)-6-hydroxy-2-methoxy-13-methyl-3-(trifluoromethylsulfonyloxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl acetate
  参考文献：
  名称：

  Structure elucidation by synthesis of four metabolites of the antitumor drug ENMD-1198 detected in human plasma samples

  摘要：

  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.

  DOI：

  10.1016/j.tet.2009.10.046
• 作为产物：
  描述：

  (13S,17S)-2-methoxy-13-methyl-3-(trifluoromethylsulfonyloxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl acetate 在 chromium(VI) oxide 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 2.0h， 以78%的产率得到(13S,17S)-2-methoxy-13-methyl-6-oxo-3-(trifluoromethylsulfonyloxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl acetate
  参考文献：
  名称：

  Structure elucidation by synthesis of four metabolites of the antitumor drug ENMD-1198 detected in human plasma samples

  摘要：

  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.

  DOI：

  10.1016/j.tet.2009.10.046