1-(3'-azido-3'-deoxythymidin-5'-yl) 4-[3-O-(4'-benzhydryloxy-3',3'-dimethylsuccinyl)-lup-2'(29)en-28-yl] 2,2-dimethylsuccinate | 1252258-60-8

• 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: 1-(3'-azido-3'-deoxythymidin-5'-yl) 4-[3-O-(4'-benzhydryloxy-3',3'-dimethylsuccinyl)-lup-2'(29)en-28-yl] 2,2-dimethylsuccinate
• CAS: 1252258-60-8
• 化学式: C₆₅H₈₇N₅O₁₁
• 分子量: 1114.43
• InChiKey: AASAPAAQQDEHFX-LNAJOYBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.63
• 重原子数：
  81.0
• 可旋转键数：
  17.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  218.05
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为产物：
  描述：

  2,2-二甲基琥珀酸 、 3-O-(3',3'-dimethylsuccinyl)betulin benzhydryl ester 、 齐多夫定 在 吡啶 、 4-二甲氨基吡啶 、 水 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 1-(3'-azido-3'-deoxythymidin-5'-yl) 4-[3-O-(4'-benzhydryloxy-3',3'-dimethylsuccinyl)-lup-2'(29)en-28-yl] 2,2-dimethylsuccinate 、 4-(3'-azido-3'-deoxythymidin-5'-yl) 1-[3-O-(4'-benzhydryloxy-3',3'-dimethylsuccinyl)-lup-2'(29)en-28-yl] 2,2-dimethylsuccinate
  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