(6S,13S,16R,17S)-6-hydroxy-2-methoxy-13-methyl-6,8,9,11,12,13,14,15,16,17-decahydro-7H-20-oxa-cyclopropa[16,17]cyclopenta[a]phenanthrene-3-carboxylic acid amide | 1204770-22-8

• 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: (6S,13S,16R,17S)-6-hydroxy-2-methoxy-13-methyl-6,8,9,11,12,13,14,15,16,17-decahydro-7H-20-oxa-cyclopropa[16,17]cyclopenta[a]phenanthrene-3-carboxylic acid amide
• 英文别名: (1R,2S,4R,6S,7S,10S,17S)-17-hydroxy-13-methoxy-7-methyl-5-oxapentacyclo[8.8.0.02,7.04,6.011,16]octadeca-11,13,15-triene-14-carboxamide
• CAS: 1204770-22-8
• 化学式: C₂₀H₂₅NO₄
• 分子量: 343.423
• InChiKey: SZEXGSVNTCOHLH-CWOQTZDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  85.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (6S,13R)-6-hydroxy-2-methoxy-13-methyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthrene-3-carboxamide 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以95%的产率得到(6S,13S,16R,17S)-6-hydroxy-2-methoxy-13-methyl-6,8,9,11,12,13,14,15,16,17-decahydro-7H-20-oxa-cyclopropa[16,17]cyclopenta[a]phenanthrene-3-carboxylic acid amide
  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

文献信息

• 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.