1-(3'-azido-3'-deoxythymidin-5'-yl) 4-[3-O-(3',3'-dimethylsuccinyl)-lup-28-yl] 2,2-dimethylsuccinate | 1252258-79-9

• 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-(3',3'-dimethylsuccinyl)-lup-28-yl] 2,2-dimethylsuccinate
• 英文别名: 4-[[(1S,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-[[4-[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]-3,3-dimethyl-4-oxobutanoyl]oxymethyl]-5a,5b,8,8,11a-pentamethyl-1-propan-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid
• CAS: 1252258-79-9
• 化学式: C₅₂H₇₉N₅O₁₁
• 分子量: 950.226
• InChiKey: XQZHDVBTSAKHEW-VBUSZLFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.1
• 重原子数：
  68
• 可旋转键数：
  17
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  189
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  2,2-二甲基琥珀酸 、 3-O-(3',3'-dimethylsuccinyl)dihydrobetulin benzhydryl ester 、 齐多夫定 在 吡啶 、 4-二甲氨基吡啶 、 水 作用下， 生成 1-(3'-azido-3'-deoxythymidin-5'-yl) 4-[3-O-(3',3'-dimethylsuccinyl)-lup-28-yl] 2,2-dimethylsuccinate 、 4-(3'-azido-3'-deoxythymidin-5'-yl) 1-[3-O-(3',3'-dimethylsuccinyl)-lup-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

文献信息

• Conjugates of betulin derivatives with AZT as potent anti-HIV agents
  作者：Juan Xiong、Yoshiki Kashiwada、Chin-Ho Chen、Keduo Qian、Susan L. Morris-Natschke、Kuo-Hsiung Lee、Yoshihisa Takaishi

  DOI：10.1016/j.bmc.2010.06.092

  日期：2010.9

  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.