Articles

Synthesis and Biological Activities of Novel Substituted-pyrazole 1,2,4-Triazolo[3,4-b]benzothiazole

  • Yao Mingxing ,
  • An Yue ,
  • Yan Jie ,
  • Tian Xing ,
  • Wei Shi
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  • a School of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029;
    b Analysis and Inspection Center, Liaoning Normal University, Dalian 116029;
    c School of Life Sciences, Liaoning Normal University, Dalian 116029

Received date: 2012-10-11

  Revised date: 2013-01-17

  Online published: 2013-01-21

Supported by

Project supported by the Fund of Liaoning Provincial Department of Education (No. 2008349).

Abstract

Twenty-one new derivatives have been synthesized using 3-substituted-4-amino-5-mercapto-1,2,4-triazale and pyrazole carboxylic acid as the staring materials. The structures of the title compounds were characterized by IR, 1H NMR and elemental analyses. The wheat gemma method preliminary bioassay results indicated that some compounds display herbicidal activity to some extent, and bacteriostatic activity test results show that the part of compounds show excellent fungicidal activity, particularly compounds 3g and 3h exhibit higher than the others, and were similar with chloramphenicol. The minimum inhibitory concentrations (MIC) of 3g and 3h with Escherichia coli and Staphylococcus aureus is 6.25 and 3.13 mg/L, and 12.5 and 6.25 mg/L, respectively.

Cite this article

Yao Mingxing , An Yue , Yan Jie , Tian Xing , Wei Shi . Synthesis and Biological Activities of Novel Substituted-pyrazole 1,2,4-Triazolo[3,4-b]benzothiazole[J]. Chinese Journal of Organic Chemistry, 2013 , 33(05) : 1015 -1021 . DOI: 10.6023/cjoc201210012

References

[1] Alexander, F. P.; Anatoly, T. S.; Alan, R. K. Heterocycles in Life and Society, Wiley, New York, 2011, pp. 209~246.
[2] Wang, Y.-G.; Wang, Z.-Y.; Zhao, X.-J.; Song, X.-J. Chin. J. Org. Chem. 2004, 24, 1606 (in Chinese).
(汪炎钢, 王子云, 赵新筠, 宋建新, 有机化学, 2004, 24, 1606.)
[3] Lahm, G. P.; Selby, T. P.; Freudenberger, J. H.; Stevenson, T. M.; Myer, B. J.; Gilles, S.; Simth, B. K.; Lindsey, F.; Clark, C. E.; Daniel, C. Bioorg. Med. Chem. Lett. 2005, 15, 4898.
[4] Shivarama Holla, B.; Narayana Poojary, K.; Sooryanarayana Rao, B.; Shivananda, M. K. Eur. J. Med. Chem. 2002, 37, 511.
[5] Hirpara, H. M.; Sodha, V. A.; Trivedi, A. M.; Khatri, B. L.; Parikh, A. R. Indian J. Chem. 2003, 42, 1756.
[6] Sadaf, J. G.; Suroor, A. K.; Nadeem, S. Bioorg. Med. Chem. Lett. 2012, 20, 4762.
[7] Holla, B. S.; Poojary, K. N.; Rao, B. S.; Shivananda, M. K. Eur. J. Med. Chem. 2002, 37, 511.
[8] Kolavi, G.; Hegde, V.; Khan, I.; Gadad, P. Bioorg. Med. Chem. 2006, 14, 3069.
[9] Prasad, D. J.; Ashok, M.; Karegoudar, P.; Poojary, B.; Holla, B. S.; Kumari, N. S. Eur. J. Med. Chem. 2009, 44, 551.
[10] Fan, Z.-J; Yang, Z.-K.; Zhang, H.-K.; Mi, N.; Wang, H.; Cai, F.; Zou, X.; Zheng, Q.-X.; Song, H. J. Agric. Food Chem. 2010, 58, 2630.
[11] Song, X.-J.; Wang, S.; Tan, X.-H.; Wang, Z.-Y.; Wang, Y.-G. Chin. J. Org. Chem. 2007, 27, 72 (in Chinese).
(宋新建, 王胜, 谭小红, 王子云, 汪炎钢, 有机化学, 2007, 27, 72.)
[12] Deng, X.-Q.; Song, M.-X.; Wei, C.-X.; Li, F.-N.; Quan, Z. S. Med. Chem. 2010, 6, 313.
[13] Kenneth, A. R.; Matsuura, N.; Tabuchi, F. EP 0213814, 1987 [Chem. Abstr. 1987, 107, 178600].
[14] An, Y.; Zhou, G.-H.; Xing, Y.-H.; Mu, P.-P.; Hu, J.-H. Chin. J. Org. Chem. 2008, 25, 539 (in Chinese).
(安悦, 周光华, 邢永恒, 牟萍萍, 胡皆汗, 有机化学, 2008, 25, 539.)
[15] Zhou, G.-H. M. S. Thesis, Liaoning Normal University, Dalian, 2008 (in Chinese).
(周光华, 硕士论文, 辽宁师范大学, 大连, 2008.)
[16] An, Y.; Zhang, T.; Jiang, H.; Zhang, L.; Han, J.; Yao, M.-X. Chin. J. Org. Chem. 2012, 32, 1308 (in Chinese).
(安悦, 张婷, 姜华, 张琳, 韩杰, 姚明星, 有机化学, 2012, 32, 1308.)
[17] Zhang, Z.-Y.; Li, M.; Zhao, L.; Li, M.-Z.; Liao, R.-A. Chin. J. Org. Chem. 1993, 13, 397 (in Chinese).
(张自义, 李明, 赵岚, 李正名, 廖仁安, 有机化学, 1993, 13, 397.)
[18] Gabriela, L. A.; Barbuceanu, S. F.; Gabriela, B.; Ioana, S; Gabriel, S.; Constantin, D. Eur. J. Med. Chem. 2010, 45, 6139.
[19] Kumar, S. G. V.; Prasa, R. Y.; Mallikarjuna, B. P.; Chandrashekar, S. M. Eur. J. Med. Chem. 2010, 45, 5120.
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