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Synthesis and Bioactivities of Novel 1,2,4-triazolo[1,5-a]Pyrimidine Derivatives Containing 1,2,4-triazole-5-thione Schiff Base Unit

  • Xiong Qizhong ,
  • Lin Xuanfu ,
  • Liu Junhu ,
  • Bi Liang ,
  • Bao Xiaoping
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  • Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang 550025

Received date: 2011-12-23

  Revised date: 2012-02-22

  Online published: 2012-03-29

Supported by

Project supported by the Governor’s Foundation for Excellent Talents of Science, Technology & Education of Guizhou Province (No.200817) and the Natural Science Foundation of Guizhou Province (No.20082265).

Abstract

Using 2-benzylthio-5-methyl-7-hydroxyl-1,2,4-triazolo[1,5-a]pyrimidine as starting compound, twenty novel 1,2,4-triazolo[1,5-a]pyrimidine derivatives containing 1,2,4-triazole-5-thione Schiff-base unit were synthesized through sequential reactions of etherification, hydrazinolysis, salification, cyclization and condensation. Target compounds were fully characterized by IR, 1H NMR, MS and elemental analysis. Preliminary bioassay indicated that some compounds exhibited certain fungicidal or good anti-TMV activities. At the concentration of 500 μg/mL, the inhibition rates of compounds 6b, 6f and 6p against TMV were 41%, 43% and 40%, respectively.

Cite this article

Xiong Qizhong , Lin Xuanfu , Liu Junhu , Bi Liang , Bao Xiaoping . Synthesis and Bioactivities of Novel 1,2,4-triazolo[1,5-a]Pyrimidine Derivatives Containing 1,2,4-triazole-5-thione Schiff Base Unit[J]. Chinese Journal of Organic Chemistry, 2012 , 32(07) : 1255 -1260 . DOI: 10.6023/cjoc1112231

References

[1] Chen, Q.; Zhu, X.-L.; Jiang, L.-L.; Liu, Z.-M.; Yang, G.-F. Eur. J. Med. Chem. 2008, 43, 595.
[2] Ruisi, G.; Canfora, L.; Bruno, G.; Rotondo, A.; Mastropietro, T. F.; Debbia, E. A.; Girasolo, M. A.; Megna, B. J. Organomet. Chem. 2010, 695, 546.  
[3] Tang, W.; Shi, D.-Q. J. Heterocycl. Chem. 2010, 47, 162.
[4] Chen, C.-N.; Chen, Q.; Liu, Y.-C.; Zhu, X.-L.; Niu, C.-W.; Xi, Z.; Yang, G.-F. Bioorg. Med. Chem. 2010, 18, 4897.  
[5] Zhang, N.; Ayral-Kaloustian, S.; Nguyen, T.; Afragola, J.; Hernandez, R.; Lucas, J.; Gibbons, J.; Beyer, C. J. Med. Chem. 2007, 50, 319.  
[6] Zhai, X.; Zhao, Y.-F.; Liu, Y.-J.; Zhang, Y.; Xun, F.-Q.; Liu, J.; Gong, P. Chem. Pharm. Bull. 2008, 56, 941.  
[7] Li, H.; Tatlock, J.; Linton, A.; Gonzalez, J.; Jewell, T.; Patel, L.; Ludlum, S.; Drowns, M.; Rahavendran, S. V.; Skor, H.; Hunter, R.; Shi, S. T.; Herlihy, K. J.; Parge, H.; Hickey, M.; Yu, X.; Chau, F.; Nonomiya, J.; Lewis, C. J. Med. Chem. 2009, 52, 1255.  
[8] Yu, W.; Goddard, C.; Clearfield, E.; Mills, C.; Xiao, T.; Guo, H.; Morrey, J. D.; Motter, N. E.; Zhao, K.; Block, T. M.; Cuconati, A.; Xu, X. J. Med. Chem. 2011, 54, 5660.  
[9] Zheng, Y.-G.; Xue, W.; Wei, X. Chin. Appl. Chem. 2010, 27, 1165 (in Chinese). (郑玉国, 薛伟, 魏学, 应用化学, 2010, 27, 1165.)
[10] Sun, X.-H.; Tao, Y.; Liu, Y.-F.; Jia, Y.-Q.; Chen, B.; Yang, J.-W. Chin. J. Org. Chem. 2008, 28, 155 (in Chinese). (孙晓红, 陶燕, 刘源发, 贾婴琦, 陈邦, 杨建武, 有机化学, 2008, 28, 155.)
[11] Wang, B.-L.; Shi, Y.-X.; Ma, Y.; Liu, X.-H.; Li, Y.-H.; Song, H.-B.; Li, B.-J.; Li, Z.-M. J. Agric. Food. Chem. 2010, 58, 5515.  
[12] Yin, K.; Jiang, L.-H.; Zhou, H.-X.; Huang, Y.; Xiang, J.-N. Chin. J. Org. Chem. 2008, 28, 1016 (in Chinese). (尹凯, 蒋历辉, 周后相, 黄勇, 向建南, 有机化学, 2008, 28, 1016.)
[13] Ma, Z.-H.; Liu, Z.-M.; Chen, Q. Chin. J. Org. Chem. 2008, 28, 1965 (in Chinese). (马忠华, 刘祖明, 陈琼, 有机化学, 2008, 28, 1965.)
[14] Yang, Z.-P.; Shan, S. Chin. J. Org. Chem. 2003, 23, 363 (in Chinese). (杨振平, 单尚, 有机化学, 2003, 23, 363.)
[15] Kong, F.-B.; Gao, Y.-F.; Chen, X.-L.; Li, G.-L.; Chen, J. Guangxi. Agric. Sci. 2006, 37, 148 (in Chinese). (孔凡彬, 高扬帆, 陈锡岭, 李广领, 陈军, 广西农业科学, 2006, 37, 148.)
[16] Li, S.-Z.; Wang D.-H.; Jiao, S.-M.; Chen, S.-E. Pesticide Experiment Methods-fungicide Sector, Agriculture Press of China, Beijing, 1991, p. 93 (in Chinese). (李树正, 王笃祜, 焦书梅, 程书恩, 农药实验法: 杀菌剂篇, 农业出版社, 北京, 1991, p. 93.)
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