17β-hydroxy-11β-{4-[1-methyl-3-(5-carboxypentyl)-ureido]-phenyl}-17α-(1-propinyl)-estra-4,9-dien-3-one | 1129547-99-4

• 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: 17β-hydroxy-11β-{4-[1-methyl-3-(5-carboxypentyl)-ureido]-phenyl}-17α-(1-propinyl)-estra-4,9-dien-3-one
• 英文别名: 6-[[[4-[(8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-prop-1-ynyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-11-yl]phenyl]-methylcarbamoyl]amino]hexanoic acid
• CAS: 1129547-99-4
• 化学式: C₃₅H₄₄N₂O₅
• 分子量: 572.745
• InChiKey: CAGNWRAPFLBXLB-CTBBFHLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  42
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  17β-hydroxy-11β-{4-[1-methyl-3-(5-carboxypentyl)-ureido]-phenyl}-17α-(1-propinyl)-estra-4,9-dien-3-one 、 氯甲酸异丁酯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.67h， 生成 C₄₀H₅₂N₂O₇
  参考文献：
  名称：

  Syntheses and Antigestagenic Activity of Mifepristone Derivatives

  摘要：

  A series of mifepristone derivatives with different "linker groups" in position 4' of the phenyl ring in the 11 beta-position of the steroid scaffold (2-41) have been synthesized. Their antigestagenic activites were determined in a cell-based assay (alkali phosphatase assay in T47-D breast cancer cells) and compared with that of the parent compound mifepristone. SAR and QSAR studies reveal the influence of both lipophilicity and partial charge based van der Waals surface area descriptors on biological activity. Within the series of compounds described in this study, three n-mifepristone derivatives are identified with considerably high antigestagenic activity. These compounds are regarded as useful starting materials for the synthesis of either physiologically stable or cleavable progesterone receptor-binding conjugates for therapeutic or diagnostic purposes.

  DOI：

  10.1021/jm800985z
• 作为产物：
  描述：

  17β-hydroxy-11β-{4-[1-methyl-3-(5-methoxycarbonylpentyl)-ureido]-phenyl}-17α-(1-propinyl)-estra-4,9-dien-3-one 在 硫酸 、 水 作用下， 以 四氢呋喃 为溶剂， 以47%的产率得到17β-hydroxy-11β-{4-[1-methyl-3-(5-carboxypentyl)-ureido]-phenyl}-17α-(1-propinyl)-estra-4,9-dien-3-one
  参考文献：
  名称：

  Syntheses and Antigestagenic Activity of Mifepristone Derivatives

  摘要：

  A series of mifepristone derivatives with different "linker groups" in position 4' of the phenyl ring in the 11 beta-position of the steroid scaffold (2-41) have been synthesized. Their antigestagenic activites were determined in a cell-based assay (alkali phosphatase assay in T47-D breast cancer cells) and compared with that of the parent compound mifepristone. SAR and QSAR studies reveal the influence of both lipophilicity and partial charge based van der Waals surface area descriptors on biological activity. Within the series of compounds described in this study, three n-mifepristone derivatives are identified with considerably high antigestagenic activity. These compounds are regarded as useful starting materials for the synthesis of either physiologically stable or cleavable progesterone receptor-binding conjugates for therapeutic or diagnostic purposes.

  DOI：

  10.1021/jm800985z