(1R,2S,3S,4S,5S,6R,7R,9S,10R)-2,3-diacetoxy-1-benzoyloxy-9-trans-cinnamoyloxy-4,6-dihydroxydihydro-β-agarofuran | 1214198-45-4

• 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: (1R,2S,3S,4S,5S,6R,7R,9S,10R)-2,3-diacetoxy-1-benzoyloxy-9-trans-cinnamoyloxy-4,6-dihydroxydihydro-β-agarofuran
• 英文别名: [(1S,2S,3S,4S,5R,6R,7S,9R,12R)-3,4-diacetyloxy-2,12-dihydroxy-2,6,10,10-tetramethyl-7-[(E)-3-phenylprop-2-enoyl]oxy-11-oxatricyclo[7.2.1.01,6]dodecan-5-yl] benzoate
• CAS: 1214198-45-4
• 化学式: C₃₅H₄₀O₁₁
• 分子量: 636.696
• InChiKey: NNIHOVDDAZGURH-ZAKGOMEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  46
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  155
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (1R,2S,3S,4S,5S,6R,7R,9S,10R)-2,3-diacetoxy-1-benzoyloxy-9-trans-cinnamoyloxy-4,6-dihydroxydihydro-β-agarofuran 、 乙酸酐 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以3 mg的产率得到(1R,2S,3S,4S,5S,6R,7R,9S,10R)-1-benzoyloxy-9-cinnamoyloxy-2,3,6-triacetoxy-4-hydroxy-dihydro-β-agarofuran
  参考文献：
  名称：

  Sesquiterpenes from Maytenus jelskii as Potential Cancer Chemopreventive Agents

  摘要：

  Seven new (1-4 and 7-9) sesquiterpenes with a dihydro-beta-agarofuran skeleton, along with four known compounds (5, 6, 10, and 11), have been isolated from the leaves of Maytenus jelskii. The Structures Of the new compounds were elucidated by means of spectroscopic data analysis, including ID and 2D NMR techniques, and their absolute configurations were determined by circular dichroism and chemical correlations. The compounds have been tested for their inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA). Compound 10 was found to be an effective antitumor-promoting agent and also showed a potent chemopreventive effect in in in vivo two-stage carcinogenesis model.

  DOI：

  10.1021/np900476a