28-capryloyloxybetulin

• 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: 28-capryloyloxybetulin
• 英文别名: 28-O-octanoylbetulin；28-O-octanylic acid ester of betulin；[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-1-isopropenyl-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-3a-yl]methyl octanoate；[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-3a-yl]methyl octanoate
• 化学式: C₃₈H₆₄O₃
• 分子量: 568.924
• InChiKey: CWSKUEVYULKAQP-BCOHOQHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.9
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  辛酸 、 白桦脂醇 在 三甲基氯硅烷 作用下， 反应 19.0h， 以84%的产率得到28-capryloyloxybetulin
  参考文献：
  名称：

  Synthesis of betulin derivatives and their protective effects against the cytotoxicity of cadmium

  摘要：

  The protecting effect of betulin against cadmium toxicity was investigated using 11 kinds of analogues. It was elucidated by analyzing the analogue activities that both hydroxyl groups on C-3 and C-28 and the isopropenyl group on C-19 played important roles for expressing efficient activities. In addition, the cytotoxicity of betulin was also reduced by being functionalized using the above functional group. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00172-4

文献信息

• Isolation, Structural Modification, and HIV Inhibition of Pentacyclic Lupane-Type Triterpenoids from <i>Cassine xylocarpa</i> and <i>Maytenus cuzcoina</i>
  作者：Oliver Callies、Luis M. Bedoya、Manuela Beltrán、Alejandro Muñoz、Patricia Obregón Calderón、Alex A. Osorio、Ignacio A. Jiménez、José Alcamí、Isabel L. Bazzocchi

  DOI：10.1021/np501025r

  日期：2015.5.22

  As a part of our investigation into new anti-HIV agents, we report herein the isolation, structure elucidation, and biological activity of six new (1-6) and 20 known (7-26) pentacyclic lupane-type triterpenoids from the stem of Cassine xylocarpa and root bark of Maytenus cuzcoina. Their stereo-structures were elucidated on the basis of spectroscopic and spectrometric methods, including ID and 2D NMR techniques. To gain a more complete understanding of the structural requirements for anti-HIV activity, derivatives 27-48 were prepared by chemical modification of the main secondary metabolites. Sixteen compounds from this series displayed inhibitory effects of human immunodeficiency virus type 1 replication with IC50 values in the micromolar range, highlighting compounds 12, 38, and 42 (IC50 4.08, 4.18, and 1.70 mu M, respectively) as the most promising anti-HIV agents.
• Synthesis of betulin derivatives and their protective effects against the cytotoxicity of cadmium
  作者：K Hiroya

  DOI：10.1016/s0968-0896(02)00172-4

  日期：2002.10

  The protecting effect of betulin against cadmium toxicity was investigated using 11 kinds of analogues. It was elucidated by analyzing the analogue activities that both hydroxyl groups on C-3 and C-28 and the isopropenyl group on C-19 played important roles for expressing efficient activities. In addition, the cytotoxicity of betulin was also reduced by being functionalized using the above functional group. (C) 2002 Elsevier Science Ltd. All rights reserved.