2,2-Dimethyl-succinic acid 4-((1S,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-hydroxymethyl-1-isopropyl-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysen-9-yl) ester

• 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: 2,2-Dimethyl-succinic acid 4-((1S,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-hydroxymethyl-1-isopropyl-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysen-9-yl) ester
• 英文别名: 4-[[(1S,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(hydroxymethyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-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-oxo-butanoic acid；4-[[(1S,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(hydroxymethyl)-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
• 化学式: C₃₆H₆₀O₅
• 分子量: 572.869
• InChiKey: UWLCHHQWRPPGFB-RKBIRBBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  41
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  二苯基重氮甲烷 、 2,2-Dimethyl-succinic acid 4-((1S,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-hydroxymethyl-1-isopropyl-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysen-9-yl) ester 以 甲醇 、 二氯甲烷 为溶剂， 以100%的产率得到3-O-(3',3'-dimethylsuccinyl)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
• 作为产物：
  描述：

  白桦脂醇 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 氢气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2,2-Dimethyl-succinic acid 4-((1S,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-hydroxymethyl-1-isopropyl-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysen-9-yl) ester
  参考文献：
  名称：

  3-O-Glutaryl-dihydrobetulin and related monoacyl derivatives as potent anti-HIV agents

  摘要：

  3-O-Acyl-betulin and -dihydrobetulin derivatives were prepared and evaluated for anti-HIV activity. 3-O-Glutaryl-dihydrobetulin (17) demonstrated extremely potent anti-HIV activity with an EC50 value of 2 x 10(-5) muM and a TI value of 1.12 x 10(6). 3-O-(3',3'-Dimethylsuccinyl)- and 3-O-(3',3'-dimethylglutaryl)-dihydrobetulins (15, 16) were also potent anti-HIV compounds with EC50 values of 0.0017 and 0.0013 muM, respectively, and TI values of 16,160 and 19,530, respectively. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.09.033

文献信息

• 3-O-Glutaryl-dihydrobetulin and related monoacyl derivatives as potent anti-HIV agents
  作者：Yoshiki Kashiwada、Michiko Sekiya、Yasumasa Ikeshiro、Toshihiro Fujioka、Nicole R. Kilgore、Carl T. Wild、Graham P. Allaway、Kuo-Hsiung Lee

  DOI：10.1016/j.bmcl.2004.09.033

  日期：2004.12

  3-O-Acyl-betulin and -dihydrobetulin derivatives were prepared and evaluated for anti-HIV activity. 3-O-Glutaryl-dihydrobetulin (17) demonstrated extremely potent anti-HIV activity with an EC50 value of 2 x 10(-5) muM and a TI value of 1.12 x 10(6). 3-O-(3',3'-Dimethylsuccinyl)- and 3-O-(3',3'-dimethylglutaryl)-dihydrobetulins (15, 16) were also potent anti-HIV compounds with EC50 values of 0.0017 and 0.0013 muM, respectively, and TI values of 16,160 and 19,530, respectively. (C) 2004 Elsevier Ltd. All rights reserved.
• 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.