4-hydroxy-3-nitrobenzyl (3S,3'R,3a'S,6aS,6bS,6'S,7a'R,9R,11aS,11bR)-3-hydroxy-3',6',10,11b-tetramethyl-1,2,3,3',3a',4,5',6,6a,6b,6',7,7',7a',8,11,11a,11b-octadecahydro-4'H-spiro[benzo[a]fluorene-9,2'-furo[3,2-b]pyridine]-4'-carboxylate | 1224886-42-3

• 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: 4-hydroxy-3-nitrobenzyl (3S,3'R,3a'S,6aS,6bS,6'S,7a'R,9R,11aS,11bR)-3-hydroxy-3',6',10,11b-tetramethyl-1,2,3,3',3a',4,5',6,6a,6b,6',7,7',7a',8,11,11a,11b-octadecahydro-4'H-spiro[benzo[a]fluorene-9,2'-furo[3,2-b]pyridine]-4'-carboxylate
• CAS: 1224886-42-3
• 化学式: C₃₅H₄₆N₂O₇
• 分子量: 606.759
• InChiKey: SGCZUZIDKKWPSH-ZJNMLKMNSA-N

物化性质

• 沸点：
  739.0±60.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.66
• 重原子数：
  44.0
• 可旋转键数：
  3.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  122.37
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4-hydroxy-3-nitrobenzyl (3S,3'R,3a'S,6aS,6bS,6'S,7a'R,9R,11aS,11bR)-3-hydroxy-3',6',10,11b-tetramethyl-1,2,3,3',3a',4,5',6,6a,6b,6',7,7',7a',8,11,11a,11b-octadecahydro-4'H-spiro[benzo[a]fluorene-9,2'-furo[3,2-b]pyridine]-4'-carboxylate 在 水 作用下， 生成 4-羟基-3-硝基苄醇 、 环巴胺
  参考文献：
  名称：

  Study of a cyclopamine glucuronide prodrug for the selective chemotherapy of glioblastoma

  摘要：

  The first glucuronide prodrug of the hedgehog signaling inhibitor cyclopamine was synthesized. The carbamoyl derivatisation of cyclopamine significantly decreased its toxicity towards the U87 human glioblastoma cell line. However, when the prodrug was incubated with beta-glucuronidase in the culture media, the active drug was efficiently released thereby restoring its anti-proliferative activity. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.12.067
• 作为产物：
  描述：

  (2S,3S,4S,5R,6S)-6-[4-[[(3S,3'R,3'aS,6'S,6aS,6bS,7'aR,9R,11aS,11bR)-3-hydroxy-3',6',10,11b-tetramethylspiro[2,3,4,6,6a,6b,7,8,11,11a-decahydro-1H-benzo[a]fluorene-9,2'-3,3a,5,6,7,7a-hexahydrofuro[3,2-b]pyridine]-4'-carbonyl]oxymethyl]-2-nitrophenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid 在 Escherichia coli β-glucuronidase 、 水 作用下， 生成 D-吡喃葡萄糖醛酸 、 4-hydroxy-3-nitrobenzyl (3S,3'R,3a'S,6aS,6bS,6'S,7a'R,9R,11aS,11bR)-3-hydroxy-3',6',10,11b-tetramethyl-1,2,3,3',3a',4,5',6,6a,6b,6',7,7',7a',8,11,11a,11b-octadecahydro-4'H-spiro[benzo[a]fluorene-9,2'-furo[3,2-b]pyridine]-4'-carboxylate
  参考文献：
  名称：

  Study of a cyclopamine glucuronide prodrug for the selective chemotherapy of glioblastoma

  摘要：

  The first glucuronide prodrug of the hedgehog signaling inhibitor cyclopamine was synthesized. The carbamoyl derivatisation of cyclopamine significantly decreased its toxicity towards the U87 human glioblastoma cell line. However, when the prodrug was incubated with beta-glucuronidase in the culture media, the active drug was efficiently released thereby restoring its anti-proliferative activity. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.12.067