Chin. J. Org. Chem. ›› 2011, Vol. 31 ›› Issue (04): 572-576. Previous Articles     Next Articles

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N-[5-(E)-1,3,4-噻二唑-2-基]-N -芳基脲的合成、晶体结构及生物活性

宋新建*,1,2,王发松1,李世荣1,胡卫兵1,汪焱钢2   

  1. (1湖北民族学院生物资源保护与利用湖北省重点实验室 恩施 445000)
    (2华中师范大学化学学院 武汉 430079)
  • 收稿日期:2010-08-02 修回日期:2010-11-17 发布日期:2010-12-03
  • 通讯作者: 宋新建 E-mail:whxjsong@139.com

Synthesis, Crystal Structure and Biological Activity of N-[5-(E)-Styryl-1,3,4-thiadiazol-2-yl]-N -arylureas

Song Xinjian*,1,2 Wang Fasong1 Li Shirong1 Hu Weibing1 Wang Yangang2   

  1. (1 Key Laboratory of Biological Resources Protection and Utilization of Hubei Province, Hubei University for Nationalities, Enshi 445000)
    (2 College of Chemistry, Central China Normal University, Wuhan 430079)
  • Received:2010-08-02 Revised:2010-11-17 Published:2010-12-03
  • Contact: Xin JianSong E-mail:whxjsong@139.com

With the aim of searching for highly bioactive urea-type cytokinins, eleven novel arylurea derivatives containing a 1,3,4-thiadiazole group were synthesized by the reaction of 2-amino-5-(E)-styryl- 1,3,4-thiadiazole with aroyl azides, which were efficiently prepared directly from their respective carboxylic acids, phosphorous oxychloride and sodium azide by one-pot procedure, then underwent a Curtius rearrangement upon heating to form the corresponding isocyanates. The structures of these title compounds were characterized by IR, 1H NMR, MS techniques and elemental analysis, and the crystal structure of 3g was determined by X-ray single crystal diffraction method. The preliminary bioassay showed that some title compounds exhibit good cytokinin activity at the concentration of 10 mg/L, especially the promoting rate of compound 3c reach above 50%.

Key words: 1,3,4-thiadiazole, acyl azide, urea, synthesis, crystal structure, cytokinin