3-O-(3',3'-dimethylsuccinyl)-28-O-tritylbetulin | 677350-28-6

• 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: 3-O-(3',3'-dimethylsuccinyl)-28-O-tritylbetulin
• CAS: 677350-28-6
• 化学式: C₅₅H₇₂O₅
• 分子量: 813.174
• InChiKey: KQIXJVSTOJCZCD-SFYHTADVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.07
• 重原子数：
  60.0
• 可旋转键数：
  11.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-O-(3',3'-dimethylsuccinyl)-28-O-tritylbetulin 在 4-甲基苯磺酸吡啶 、 水 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 以58.9%的产率得到2,2-Dimethyl-succinic acid 4-((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-hydroxymethyl-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysen-9-yl) 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
• 作为产物：
  描述：

  2,2-二甲基琥珀酸 、 28-O-tritylbetulin 在 吡啶 、 4-二甲氨基吡啶 、 水 作用下， 以38.9%的产率得到3-O-(3',3'-dimethylsuccinyl)-28-O-tritylbetulin
  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