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有机化学 ›› 2008, Vol. 28 ›› Issue (10): 1826-1829. 上一篇    下一篇

研究简报

14-羟基菲并[9,10,3’,4’]吲哚里西啶的合成及生物活性研究

王开亮; 汪清民*; 黄润秋   

  1. (南开大学元素有机化学研究所 元素有机化学国家重点实验室 天津 300071)
  • 收稿日期:2008-03-29 修回日期:2008-05-09 发布日期:2008-10-20
  • 通讯作者: 汪清民

Synthesis of 14-Hydroxyphenanthro[9,10,3’,4’]indolizidine and Its Biological Activities

WANG, Kai-Liang; WANG, Qing-Min*; HUANG, Run-Qiu   

  1. (State Key Laboratory of Elemento-organic Chemistry, Institute of Elemento-organic Chemistry,
    Nankai University, Tianjin 300071)
  • Received:2008-03-29 Revised:2008-05-09 Published:2008-10-20
  • Contact: WANG, Qing-Min

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以吡咯为起始原料, 以三氟氧钒(VOF3)氧化偶联重排反应为关键步骤, 经过7步反应, 合成了结构骨架全新的14-羟基菲并[9,10,3’,4’]吲哚里西啶化合物8, 总收率为55%. 采用1H NMR, 13C NMR, IR, MS和HRMS对中间体和目标产物进行了表征. 初步的抗烟草花叶病毒生物活性测试结果表明, 目标化合物8对烟草花叶病毒无明显抑制作用, 但具有较好的抗肿瘤活性, 中间体9-氧代-14-羟基-14a-甲氧基菲并[9,10,3’,4’]吲哚里西啶化合物7却表现出了很好的抗烟草花叶病毒活性.

关键词: 三氟氧钒, 菲并吲哚里西啶, 抗肿瘤活性, 烟草花叶病毒

A new compound, 14-hydroxyphenanthro[9,10,3’,4’]indolizidine (8), has been synthesized utilizing pyrrole as starting material via the oxidative coupling and rearrangement reactions by vanadium oxytrifluoride (VOF3) in seven steps in an overall yield 55%. The structures of the target compound and its precursors were confirmed by 1H NMR, 13C NMR, IR, MS and HRMS techniques. Preliminary bioassay showed that 8 had weak antiviral activity against tobacco mosic virus (TMV), but exhibited potential antitumour activity. The intermediate 9-oxo-14-hydroxy-14a-methoxyphenanthro[9,10,3’,4’]indolizidine (7) exhibited excellent anti-viral activity against TMV.

Key words: phenanthroindolizidine, vanadium oxytrifluoride, tobacco mosic virus (TMV), antitumour activity