28-O-β-glucuronide betulinic acid | 1125546-06-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 28-O-β-glucuronide betulinic acid
• 英文别名: (2S,3S,4S,5R,6S)-6-[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carbonyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 1125546-06-6
• 化学式: C₃₆H₅₆O₉
• 分子量: 632.835
• InChiKey: JWYRZWZMCRZRHJ-CHTCPWBTSA-N

物化性质

• 沸点：
  720.7±60.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  45
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  154
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  28-O-β-glucuronide betulinic acid 在 Escherichia coli β-D-glucuronidase 作用下， 反应 1.0h， 生成 白桦脂酸
  参考文献：
  名称：

  Synthesis of betulinic acid acyl glucuronide for application in anticancer prodrug monotherapy

  摘要：

  The synthesis of 28-O-beta-D-glucuronide betulinic acid, an acyl glucuronide derivative, was successfully carried out for the first time using commercially available peracetylated methyl glucuronate bromide under phase-transfer conditions. The target compound could be used in an anticancer prodrug monotherapy (PMT) strategy since it is non-cytotoxic, non-haemolytic, more water soluble than betulinic acid, it possesses a good in vitro stability in phosphate buffer and can be hydrolyzed in the presence of beta-D-glucuronidase releasing in vitro betulinic acid, a promising anticancer agent. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.12.043
• 作为产物：
  描述：

  28-O-(methy-2,3,4-tri-acetyl-β-D-glucuronate) betulinic acid 在 氢氧化钾 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.5h， 以76%的产率得到28-O-β-glucuronide betulinic acid
  参考文献：
  名称：

  Synthesis of betulinic acid acyl glucuronide for application in anticancer prodrug monotherapy

  摘要：

  The synthesis of 28-O-beta-D-glucuronide betulinic acid, an acyl glucuronide derivative, was successfully carried out for the first time using commercially available peracetylated methyl glucuronate bromide under phase-transfer conditions. The target compound could be used in an anticancer prodrug monotherapy (PMT) strategy since it is non-cytotoxic, non-haemolytic, more water soluble than betulinic acid, it possesses a good in vitro stability in phosphate buffer and can be hydrolyzed in the presence of beta-D-glucuronidase releasing in vitro betulinic acid, a promising anticancer agent. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.12.043

文献信息

• Synthesis of betulinic acid acyl glucuronide for application in anticancer prodrug monotherapy
  作者：Charles Gauthier、Jean Legault、Simon Rondeau、André Pichette

  DOI：10.1016/j.tetlet.2008.12.043

  日期：2009.3

  The synthesis of 28-O-beta-D-glucuronide betulinic acid, an acyl glucuronide derivative, was successfully carried out for the first time using commercially available peracetylated methyl glucuronate bromide under phase-transfer conditions. The target compound could be used in an anticancer prodrug monotherapy (PMT) strategy since it is non-cytotoxic, non-haemolytic, more water soluble than betulinic acid, it possesses a good in vitro stability in phosphate buffer and can be hydrolyzed in the presence of beta-D-glucuronidase releasing in vitro betulinic acid, a promising anticancer agent. (C) 2008 Elsevier Ltd. All rights reserved.