30-O-acetyl-3-oxo-lup-20(29)-ene | 79875-82-4

• 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: 30-O-acetyl-3-oxo-lup-20(29)-ene
• 英文别名: 2-[(1R,3aR,5aR,5bR,7aR,11aR,11bR,13aR,13bS)-3a,5a,5b,8,8,11a-hexamethyl-9-oxo-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysen-1-yl]allyl acetate；2-[(1R,3aR,5aR,5bR,7aR,11aR,11bR,13aR,13bS)-3a,5a,5b,8,8,11a-hexamethyl-9-oxo-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysen-1-yl]prop-2-enyl acetate
• CAS: 79875-82-4
• 化学式: C₃₂H₅₀O₃
• 分子量: 482.747
• InChiKey: KINMTOIILIBWGA-BDNLLUJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙酸酐 、 30-羟基羽扇-20(29)-烯-3-酮 在 吡啶 作用下， 反应 0.08h， 以18 mg的产率得到30-O-acetyl-3-oxo-lup-20(29)-ene
  参考文献：
  名称：

  3-Oxolup-20（29）-en-30-al，一种来自Gymnosporia emarginata（Celastraceae）的新卢烷

  摘要：

  Gymnosporia emarginata（Willd。）钩的树皮f。前任。THW。（Celastraceae）包含许多三萜类化合物，包括新的氧化的双氧戊烷，3-oxolup-20（29）-en-30-al（1）和两个相关的羽扇豆，3β-hydroxylup-20（29）-en-30-al （2）和30-hydroxylup-20（29）-en-3-one（3）。这些化合物的结构已经通过光谱和化学方法确定。

  DOI：

  10.1039/p19810002724

文献信息

• 3-Oxolup-20(29)-en-30-al, a new lupane from Gymnosporia emarginata(Celastraceae)
  作者：Dharmassree B. T. Wijeratne、Vijaya Kumar、M. Uvais S. Sultanbawa

  DOI：10.1039/p19810002724

  日期：——

  The stem bark of Gymnosporia emarginata(Willd.) Hook f. ex. Thw. (Celastraceae) contains a number of triterpenes including a new oxygenated lupane, 3-oxolup-20(29)-en-30-al (1) and two related lupanes, 3β-hydroxylup-20(29)-en-30-al (2) and 30-hydroxylup-20(29)-en-3-one (3). The structures of these compounds have been established by spectroscopic and chemical methods.

  Gymnosporia emarginata（Willd。）钩的树皮f。前任。THW。（Celastraceae）包含许多三萜类化合物，包括新的氧化的双氧戊烷，3-oxolup-20（29）-en-30-al（1）和两个相关的羽扇豆，3β-hydroxylup-20（29）-en-30-al （2）和30-hydroxylup-20（29）-en-3-one（3）。这些化合物的结构已经通过光谱和化学方法确定。
• 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.