4-[[(3S,5R,6S,8R,9R,10R,12R,13R,14R,17S)-3,12-dihydroxy-4,4,8,10,14-pentamethyl-17-[(2R)-2,6,6-trimethyloxan-2-yl]-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid | 1160164-72-6

• 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: 4-[[(3S,5R,6S,8R,9R,10R,12R,13R,14R,17S)-3,12-dihydroxy-4,4,8,10,14-pentamethyl-17-[(2R)-2,6,6-trimethyloxan-2-yl]-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid
• CAS: 1160164-72-6
• 化学式: C₃₆H₆₀O₇
• 分子量: 604.868
• InChiKey: GGMOUZLNXHMKPT-JXGRFAEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  43
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,2-二甲基琥珀酸酐 、 panaxatriol 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 16.0h， 以31.4%的产率得到4-[[(3S,5R,6S,8R,9R,10R,12R,13R,14R,17S)-6,12-dihydroxy-4,4,8,10,14-pentamethyl-17-[(2R)-2,6,6-trimethyloxan-2-yl]-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid
  参考文献：
  名称：

  Synthesis of dammarane-type triterpene derivatives and their ability to inhibit HIV and HCV proteases

  摘要：

  We synthesized dammarane-type triterpene derivatives and evaluated their ability to inhibit HIV-1 and HCV proteases to understand their structure-activity relationships. All of the mono- and di-succinyl derivatives (5a-5f) were powerful inhibitors of HIV-1 protease (IC50 < 10 mu M). However, only di-succinyl (5e) and 2,3-seco-2,3-dioic acid (3b) derivatives similarly inhibited HCV protease (IC50 < 10 mu M). A-nor dammarane- type triterpenes (4a and 4b, IC50 10.0 and 29.9 mu M, respectively) inhibited HIV-1 protease moderately or strongly, but were inactive against HCV protease. All compounds that powerfully inhibited HIV-1 or HCV protease did not appreciably inhibit the general human proteases, renin and trypsin (IC50 > 1000 mu M). These findings indicated that the mono-succinyl dammarane type derivatives (5a-5d) selectively inhibited HIV-1 protease and that the di-succinyl (5e, 5f) as well as 2,3-seco-2,3-dioic acid (3b) derivatives preferably inhibited both viral proteases. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.03.019

文献信息

• Synthesis of dammarane-type triterpene derivatives and their ability to inhibit HIV and HCV proteases
  作者：Ying Wei、Chao-Mei Ma、Masao Hattori

  DOI：10.1016/j.bmc.2009.03.019

  日期：2009.4

  We synthesized dammarane-type triterpene derivatives and evaluated their ability to inhibit HIV-1 and HCV proteases to understand their structure-activity relationships. All of the mono- and di-succinyl derivatives (5a-5f) were powerful inhibitors of HIV-1 protease (IC50 < 10 mu M). However, only di-succinyl (5e) and 2,3-seco-2,3-dioic acid (3b) derivatives similarly inhibited HCV protease (IC50 < 10 mu M). A-nor dammarane- type triterpenes (4a and 4b, IC50 10.0 and 29.9 mu M, respectively) inhibited HIV-1 protease moderately or strongly, but were inactive against HCV protease. All compounds that powerfully inhibited HIV-1 or HCV protease did not appreciably inhibit the general human proteases, renin and trypsin (IC50 > 1000 mu M). These findings indicated that the mono-succinyl dammarane type derivatives (5a-5d) selectively inhibited HIV-1 protease and that the di-succinyl (5e, 5f) as well as 2,3-seco-2,3-dioic acid (3b) derivatives preferably inhibited both viral proteases. (C) 2009 Elsevier Ltd. All rights reserved.