3-O-glutaryl-dihydrobetulin benzhydryl ester | 1252258-44-8

• 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: 3-O-glutaryl-dihydrobetulin benzhydryl ester
• CAS: 1252258-44-8
• 化学式: C₄₈H₆₈O₅
• 分子量: 725.065
• InChiKey: BUIKPFFYJVASDD-YLZPNGCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.13
• 重原子数：
  53.0
• 可旋转键数：
  10.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  戊二酸酐 、 3-O-glutaryl-dihydrobetulin benzhydryl ester 在 吡啶 、 4-二甲氨基吡啶 、 水 作用下， 以94.9%的产率得到3-O-(5'-benzhydryloxyglutaryl)-28-O-glutaryldihydrobetulin
  参考文献：
  名称：

  Conjugates of betulin derivatives with AZT as potent anti-HIV agents

  摘要：

  Fourteen novel conjugates of 3,28-di-O-acylbetulins with AZT were prepared as anti-HIV agents, based on our previously reported potent anti-HIV triterpene leads, including 3-O-acyl and 3,28-di-O-acylbetulins. Nine of the conjugates (49-53, 55, 56, 59, and 60) exhibited potent anti-HIV activity at the submicromolar level, with EC(50) values ranging from 0.040 to 0.098 mu M in HIV-1(NL4-3) infected MT-4 cells. These compounds were equipotent or more potent than 3-O-(3',3'-dimethylsuccinyl) betulinic acid (2), which is currently in Phase IIb anti-AIDS clinical trial. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.092
• 作为产物：
  描述：

  二苯基重氮甲烷 、 3-O-glutaryl-dihydrobetulin 以 甲醇 、 二氯甲烷 为溶剂， 以96.4%的产率得到3-O-glutaryl-dihydrobetulin benzhydryl ester
  参考文献：
  名称：

  Conjugates of betulin derivatives with AZT as potent anti-HIV agents

  摘要：

  Fourteen novel conjugates of 3,28-di-O-acylbetulins with AZT were prepared as anti-HIV agents, based on our previously reported potent anti-HIV triterpene leads, including 3-O-acyl and 3,28-di-O-acylbetulins. Nine of the conjugates (49-53, 55, 56, 59, and 60) exhibited potent anti-HIV activity at the submicromolar level, with EC(50) values ranging from 0.040 to 0.098 mu M in HIV-1(NL4-3) infected MT-4 cells. These compounds were equipotent or more potent than 3-O-(3',3'-dimethylsuccinyl) betulinic acid (2), which is currently in Phase IIb anti-AIDS clinical trial. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.092