3-O-(3',3'-Dimethyl)-succinyl-ursolic acid

• 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'-Dimethyl)-succinyl-ursolic acid
• 英文别名: (1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-(3-carboxy-3-methylbutanoyl)oxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
• 化学式: C₃₆H₅₆O₆
• 分子量: 584.837
• InChiKey: KSXVQSFQASMLRX-KVVGEXSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  42
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,2-二甲基琥珀酸酐 、 熊果酸 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 生成 3-O-(3',3'-Dimethyl)-succinyl-ursolic acid 、 3-O-(2',2'-Dimethylsuccinyl)-ursolic acid
  参考文献：
  名称：

  Anti-AIDS Agents 38. Anti-HIV Activity of 3-O-Acyl Ursolic Acid Derivatives

  摘要：

  Based on our previous finding that 3-O-acyl-betulinic and -oleanolic acids, especially the 3-O-(3',3'-dimethyl)-succinyl derivatives (2 and 4), demonstrated potent anti-HIV activity [EC50 < 0.00035 and 0.00086 M; therapeutic index (TI) > 20 000 and 22 326, respectively], several 3-O-acyl-ursolic acids were prepared and evaluated for anti-HIV activity. Ursolic acid (6) was equipotent (EC50 4.4 muM) with oleanolic acid (EC50 3.7 muM), although it was slightly toxic (IC50 14.3 CIM, TI 3.3). 3-O-Diglycoryl-ursolic acid (10) demonstrated relatively potent anti-HIV activity with an EC50 of 0.31 muM and a TI of 155.5. In contrast, 3-O-(3',3'-dimethylsuccinyl)-ursolic acid (8), which is analogous to the extremely potent anti-HIV betulinic acid and oleanolic acid derivatives 2 and 4, displayed only weak anti-HIV activity (EC50 2.1 muM, TI 23.6).

  DOI：

  10.1021/np990633v

文献信息

• Anti-AIDS Agents 38. Anti-HIV Activity of 3-<i>O</i>-Acyl Ursolic Acid Derivatives
  作者：Yoshiki Kashiwada、Tsuneatsu Nagao、Ayumi Hashimoto、Yasumasa Ikeshiro、Hikaru Okabe、L. Mark Cosentino、Kuo-Hsiung Lee

  DOI：10.1021/np990633v

  日期：2000.12.1

  Based on our previous finding that 3-O-acyl-betulinic and -oleanolic acids, especially the 3-O-(3',3'-dimethyl)-succinyl derivatives (2 and 4), demonstrated potent anti-HIV activity [EC50 < 0.00035 and 0.00086 M; therapeutic index (TI) > 20 000 and 22 326, respectively], several 3-O-acyl-ursolic acids were prepared and evaluated for anti-HIV activity. Ursolic acid (6) was equipotent (EC50 4.4 muM) with oleanolic acid (EC50 3.7 muM), although it was slightly toxic (IC50 14.3 CIM, TI 3.3). 3-O-Diglycoryl-ursolic acid (10) demonstrated relatively potent anti-HIV activity with an EC50 of 0.31 muM and a TI of 155.5. In contrast, 3-O-(3',3'-dimethylsuccinyl)-ursolic acid (8), which is analogous to the extremely potent anti-HIV betulinic acid and oleanolic acid derivatives 2 and 4, displayed only weak anti-HIV activity (EC50 2.1 muM, TI 23.6).