1-O-[(8-苯胺基-8-氧代辛酰)氨基]-beta-D-吡喃葡萄糖醛酸 | 863456-50-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-O-[(8-苯胺基-8-氧代辛酰)氨基]-beta-D-吡喃葡萄糖醛酸
• 中文别名: (辛二酰苯胺异羟肟酸)-&Beta-D-葡糖苷酸；(辛二酰苯胺异羟肟酸)-Β-D-葡糖苷酸
• 英文名称: Vorinostat O-Glucuronide
• 英文别名: Vorinostat-o-glucuronide；(2S,3S,4S,5R,6S)-6-[(8-anilino-8-oxooctanoyl)amino]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 863456-50-2
• 化学式: C₂₀H₂₈N₂O₉
• 分子量: 440.45
• InChiKey: AGXZHORDQQELAH-JNIAIEOXSA-N

物化性质

• 熔点：
  188-190°C
• 密度：
  1.41±0.1 g/cm3(Predicted)
• 溶解度：
  溶于甲醇、水

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  175
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  乙酰溴-Alpha-D-葡萄糖酮酸甲基酯 在 sodium hydroxide 、 sodium methylate 、 四丁基硫酸氢铵 、 sodium carbonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 肼 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 19.16h， 生成 1-O-[(8-苯胺基-8-氧代辛酰)氨基]-beta-D-吡喃葡萄糖醛酸
  参考文献：
  名称：

  Synthesis and biological evaluation of the suberoylanilide hydroxamic acid (SAHA) β-glucuronide and β-galactoside for application in selective prodrug chemotherapy

  摘要：

  The beta-O-glucuronide and beta-O-galactoside of SAHA have been prepared and evaluated as prodrugs for selective cancer chemotherapy (ADEPT, PMT). These new compounds are stable under physiological conditions and do not exhibit any antiproliferative activity compared to the parent drug after a 48-h treatment of H661 cells. The glucuronide derivative did not lead to the release of the drug in the presence of either Escherichia coli or bovine liver beta-glucuronidase. On the other hand, under enzymatic cleavage of galactoside prodrug by the corresponding enzyme, a rapid release of SARA was observed demonstrating that the beta-O-galactoside of SAHA is a promising candidate for in vivo investigations. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.042

文献信息

• Synthesis and biological evaluation of the suberoylanilide hydroxamic acid (SAHA) β-glucuronide and β-galactoside for application in selective prodrug chemotherapy
  作者：Mickaël Thomas、Freddy Rivault、Isabelle Tranoy-Opalinski、Joëlle Roche、Jean-Pierre Gesson、Sébastien Papot

  DOI：10.1016/j.bmcl.2006.11.042

  日期：2007.2

  The beta-O-glucuronide and beta-O-galactoside of SAHA have been prepared and evaluated as prodrugs for selective cancer chemotherapy (ADEPT, PMT). These new compounds are stable under physiological conditions and do not exhibit any antiproliferative activity compared to the parent drug after a 48-h treatment of H661 cells. The glucuronide derivative did not lead to the release of the drug in the presence of either Escherichia coli or bovine liver beta-glucuronidase. On the other hand, under enzymatic cleavage of galactoside prodrug by the corresponding enzyme, a rapid release of SARA was observed demonstrating that the beta-O-galactoside of SAHA is a promising candidate for in vivo investigations. (c) 2006 Elsevier Ltd. All rights reserved.