Chin. J. Org. Chem. ›› 2008, Vol. 28 ›› Issue (10): 1826-1829. Previous Articles     Next Articles



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

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