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有机化学 ›› 2008, Vol. 28 ›› Issue (9): 1590-1597. 上一篇    下一篇

研究论文

5-取代氨基-12-取代苯并[c]菲啶衍生物的合成、晶体结构及生物活性

张 敏 ; 毛神杰 ; 吕 培; 谢龙观; 徐效华*   

  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:2008-01-07 修回日期:2008-03-25 发布日期:2008-09-20
  • 通讯作者: 徐效华

Synthesis, Crystal Structure and Biological Activity of 5-(Substituted amino)-12-substituent-benzo[c]phenanthridine Derivatives

ZHANG, Min; MAO, Shen-Jie; LÜ, Pei; XIE, Long-Guan; XU, Xiao-Hua*   

  1. (State Key Laboratory of Elemento-organic Chemistry, Institute of Elemento-organic Chemistry,
    Nankai University, Tianjin 300071)
  • Received:2008-01-07 Revised:2008-03-25 Published:2008-09-20
  • Contact: XU, Xiao-Hua

PDF

1336

被引次数

5

为了寻找新的高活性农药, 利用2-甲基苯甲腈与不同的醛反应, 再通过2,3-二氯-5,6-二氰基-1,4-苯醌(DDQ)脱氢或NaH和CH3I氮甲基化, 合成了3个系列共18个5-取代氨基-12-取代苯并[c]菲啶衍生物, 其中15个是未见文献报道的化合物. 它们的结构均经1H NMR, 13C NMR, IR和高分辨质谱表征; 用X射线衍射测定了化合物5-氨基-12-(4-二乙氨基苯基)-11,12-2H-苯并[c]菲啶盐酸盐(3c)的晶体结构. 初步的生物活性测试结果表明, 部分化合物具有一定的杀菌活性和促进黄瓜子叶生根活性.

关键词: 苯并[c]菲啶, 合成, 生物活性, 晶体结构

In order to find highly active pesticide, three series of 5-(substituted amino)-12-substituent- benzo[c]phenanthridine derivatives were synthesized through the reaction of 2-methylbenzonitrile with dif-ferent aldehyde, and further dehydration with DDQ or N-methylation with NaH and CH3I, respectively. Their structures were characterized by 1H NMR, 13C NMR, IR spectra and HRMS, and the structure of 5-amino-12-(4-diethylaminophenyl)-11,12-2H-benzo[c]phenanthridine hydrochloride (3c) was determined by X-ray single crystal diffraction method. The preliminary bioassay showed that some title compounds ex-hibited certain fungicidal activities and cucumber cotyledon root-formation promoting activities.

Key words: benzo[c]phenanthridine, crystal structure, biological activity, synthesis