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Journal of Structural Chemistry

, Volume 59, Issue 6, pp 1473–1477 | Cite as

Crystal Structure of a Novel 1,2,4- Triazolo[4,3-a]Pyridine Compound with Antifungal Activity

  • Q. Wang
  • Z.-W. Zhai
  • Z.-H. Sun
  • M.-Y. Yang
  • L. Han
  • X.-H. LiuEmail author
  • C.-X. Tan
  • J.-Q. Weng
Article
  • 18 Downloads

Abstract

The title compound 8-chloro-3-((4-cyanobenzyl)thio)-[1,2,4]triazolo[4,3-a]pyridine is prepared from 1- cyano-4-(chloromethyl)benzene and 8-chloro-[1,2,4]triazolo[4,3-a]pyridine-3(2H)-thione in the presence of NaOH, and its structure is determined by the X-ray diffraction analysis. The crystals are monoclinic, space group P2(1)/n, with a = 14.018(8) Å, b = 4.096(2) Å, c = 22.974(12) Å, β = 99.759(9)°, V = 1300.1(12) Å3, and Z = 4, the final R = 0.0343 and wR = 0.0788 for 2505 observed reflections with I > 2σ(I). The preliminary biological test shows that the title compound has activities against Stemphylium lycopersici (Enjoji) Yamamoto, Fusarium oxysporum. sp. cucumebrium, and Botrytis cinerea with inhibitory to be 51.19%, 62.02%, 15.56% respectively.

Keywords

1,2,4-triazolo[4,3-a]pyridine synthesis crystal structure antifungal activity 

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References

  1. 1.
    X. H. Liu, C. X. Tan, and J. Q. Weng. Phosphorus Sulfur Silicon Relat. Elem., 2011, 186, 552–557.CrossRefGoogle Scholar
  2. 2.
    X. H. Liu, W. Zhao, Z. H. Shenet, et al. Eur. J. Med. Chem., 2017, 125, 881–889.CrossRefGoogle Scholar
  3. 3.
    W. Zhao, Z. H. Shen, T. M. Xu, et al. Lett. Drug Des. Discovery, 2017, 14, 323–329.CrossRefGoogle Scholar
  4. 4.
    X. H. Liu, W. Zhao, Z. H. Shen, et al. Bioorg. Med. Chem. Lett., 2016, 26, 3626–3628.CrossRefGoogle Scholar
  5. 5.
    X. H. Liu, Q. Wang, Z. H. Sun, et al. Pest Manage. Sci., 2017, 73, 953–959.CrossRefGoogle Scholar
  6. 6.
    C. X. Tan, J. Q. Weng, Z. X. Liu, et al. Phosphorus Sulfur Silicon Relat. Elem., 2012, 187, 990–996.CrossRefGoogle Scholar
  7. 7.
    M. Ozil, O. Bodur, S. Ulker, et al. Chem. Heterocycl. Compd., 2015, 51, 88–96.CrossRefGoogle Scholar
  8. 8.
    X. H. Liu, Z. H. Sun, M. Y. Yang, et al. Chem. Biol. Drug Des., 2014, 84, 342–347.CrossRefGoogle Scholar
  9. 9.
    Z. H. Shen, Y. X. Shi, M. Y. Yang, et al. Chin. J. Struct. Chem., 2016, 35, 457–464.Google Scholar
  10. 10.
    R. P. Bhole and K. P. Bhusari. Med. Chem. Res., 2011, 20, 695–704.CrossRefGoogle Scholar
  11. 11.
    Z. H. Sun, Z. W. Zai, M. Y. Yang, et al. J. Chin. Struct. Chem., 2014, 33, 1779–1783.Google Scholar
  12. 12.
    X. H. Liu, C. X. Tan, and J. Q. Weng. Phosphorus Sulfur Silicon Relat. Elem., 2011, 186, 558–564.CrossRefGoogle Scholar
  13. 13.
    L. J. Zhang, M. Y. Yang, Z. H. Sun, et al. Lett. Drug Des. Discov., 2014, 11, 1107–1111.CrossRefGoogle Scholar
  14. 14.
    S. F. Barbuceanu, D. C. Ilies, V. Radulescu, et al. Rev. De Chim., 2014, 65, 1172–1175.Google Scholar
  15. 15.
    X. H. Liu, X. Y. Xu, C. X. Tan, et al. Pest Manag. Sci., 2015, 71, 292–301.CrossRefGoogle Scholar
  16. 16.
    X. H. Liu, Z. W. Zhai, X. Y. Xu, et al. Bioorg. Med. Chem. Lett., 2015, 25, 5524–5528.CrossRefGoogle Scholar
  17. 17.
    Z. W. Zhai, Y. X. Shi, M. Y. Yang, et al. Lett. Drug Des. Discov., 2016, 13, 521–525.CrossRefGoogle Scholar
  18. 18.
    L. P. Guan, R. P. Zhang, Y. Sun, et al. Arzneimittel Forschung Drug Res., 2016, 13, 521–525.Google Scholar
  19. 19.
    X. H. Liu, Y. M. Fang, F. Xie, et al. Pest Manag. Sci., 2017, 73, 1900–1907.CrossRefGoogle Scholar
  20. 20.
    S. L. Yan, M. Y. Yang, Z. H. Sun, et al. Lett. Drug Des. Discov., 2014, 11, 940–943.CrossRefGoogle Scholar
  21. 21.
    G. M. Sheldrich. SHELX–97, release 97–2. Germany, University of Goettingen, 1998.Google Scholar
  22. 22.
    Z. W. Zhai, Y. X. Shi, M. Y. Yang, et al. Chin. J. Struct. Chem., 2016, 35(1), 25–33.Google Scholar
  23. 23.
    S. Umezono and T. Okuno. J. Struct. Chem., 2015, 56(3), 472–474.CrossRefGoogle Scholar
  24. 24.
    Q. Wang, Z. W. Zhai, Z. H. Sun, et al. Chin. J. Struct. Chem., 2016, 35(5), 651–655.CrossRefGoogle Scholar
  25. 25.
    O. A. Maiorova, V. S. Grinev, and A. Y. Yegorova. J. Struct. Chem., 2015, 56(4), 803–805.CrossRefGoogle Scholar
  26. 26.
    M. Y. Yang, W. Zhao, X. H. Liu, et al. Chin. J. Struct. Chem., 2015, 34(2), 203–207.Google Scholar
  27. 27.
    A. Saeed, I. Arshad, and U. Floerke. J. Struct. Chem., 2015, 56(2), 396–398.CrossRefGoogle Scholar
  28. 28.
    J. J. Xia. J. Struct. Chem., 2014, 55, 130–133.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  • Q. Wang
    • 1
  • Z.-W. Zhai
    • 1
  • Z.-H. Sun
    • 1
  • M.-Y. Yang
    • 1
  • L. Han
    • 1
  • X.-H. Liu
    • 1
    Email author
  • C.-X. Tan
    • 1
  • J.-Q. Weng
    • 1
  1. 1.College of Chemical EngineeringZhejiang University of TechnologyHangzhouP.R. China

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