28-O-(methy-2,3,4-tri-acetyl-β-D-glucuronate) betulinic acid | 1125546-14-6

• 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-(methy-2,3,4-tri-acetyl-β-D-glucuronate) betulinic acid
• 英文别名: methyl (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-triacetyloxyoxane-2-carboxylate
• CAS: 1125546-14-6
• 化学式: C₄₃H₆₄O₁₂
• 分子量: 772.974
• InChiKey: JKCHGDAIGDNJST-KCAVVTECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  55
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  161
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  白桦脂酸 、 乙酰溴-Alpha-D-葡萄糖酮酸甲基酯 在 四丁基溴化铵 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 6.0h， 以76%的产率得到28-O-(methy-2,3,4-tri-acetyl-β-D-glucuronate) 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