1β-acetoxi-20(S),24(R)-epoxi-3α,12b,25-trihidroxidammarane | 651025-45-5

• 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: 1β-acetoxi-20(S),24(R)-epoxi-3α,12b,25-trihidroxidammarane
• 英文别名: 24-epi-polacandrin 3-acetate；1-Acetyl-24-epi-polacandrin；[(1R,3R,5S,8R,9S,10R,12R,13R,14R,17S)-1,12-dihydroxy-17-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 651025-45-5
• 化学式: C₃₂H₅₄O₆
• 分子量: 534.777
• InChiKey: RBYRZIJOZWZKMC-VZVZPYEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  38
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1β-acetoxi-20(S),24(R)-epoxi-3α,12b,25-trihidroxidammarane 在 jones' reagent 作用下， 以 丙酮 为溶剂， 以64%的产率得到Acetic acid (3S,5R,8S,9R,10S,13S,14S,17R)-4,4,8,10,14-pentamethyl-17-((R)-2-methyl-5-oxo-tetrahydro-furan-2-yl)-1,12-dioxo-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester
  参考文献：
  名称：

  New Dammarane Triterpenes from the Aerial Parts of Ibicella lutea Grown in Argentina

  摘要：

  Two new dammarane triterpenes have been isolated from the aerial parts of Ibicella lutea, 3-acetyl-24-epi-polacandrin (1) and 1,3-diacetyl-24-epi-polacandrin (2), and were obtained along with the known compounds 20S*,24S*-epoxy-3beta,12beta,25-trihydroxydammarane (3) and apigenin. The structures of compounds I and 2 were deduced by spectroscopic studies and by chemical transformations leading to the preparation of derivatives 4-11. The structure and relative stereochemistry of 1 were verified by single-crystal X-ray analysis. The natural compounds and selected semisynthetic derivatives were evaluated against several tumor cells.

  DOI：

  10.1021/np030273i

文献信息

• Dammarane triterpenes targeting α-synuclein: biological activity and evaluation of binding sites by molecular docking
  作者：Alberto Cornejo、Julio Caballero、Mario Simirgiotis、Vanessa Torres、Luisa Sánchez、Nicolás Díaz、Marcela Guimaraes、Marcos Hernández、Carlos Areche、Sergio Alfaro、Leonardo Caballero、Francisco Melo

  DOI：10.1080/14756366.2020.1851216

  日期：2021.1.1