Citation: SUN Guo-Xiang, SHI Yan-Xia, ZHAI Zhi-Wen, SUN Zhao-Hui, WENG Jian-Quan, TAN Cheng-Xia, LIU Xing-Hai, LI Bao-Ju. Synthesis, Crystal Structure and Antifungal Activity of 2-((2-Fluorobenzyl)thio)-5-(pyridin-4-yl)-1,3,4-oxadiazole[J]. Chinese Journal of Structural Chemistry, ;2016, 35(12): 1855-1859. doi: 10.14102/j.cnki.0254-5861.2011-1352 shu

Synthesis, Crystal Structure and Antifungal Activity of 2-((2-Fluorobenzyl)thio)-5-(pyridin-4-yl)-1,3,4-oxadiazole

  • Corresponding author: LIU Xing-Hai, xhliu@zjut.edu.cn LI Bao-Ju, libj@caas.cn
  • Received Date: 5 July 2016
    Accepted Date: 17 October 2016

    Fund Project: Natural Science Foundation of Zhejiang Province LY16C140007program of Science and Technology of Jiangsu Province BY2014108-14

Figures(3)

  • The title compound 2-((2-fluorobenzyl)thio)-5-(pyridin-4-yl)-1,3,4-oxadiazole (C14H10FN3OS) was synthesized, and its structure was confirmed by 1H NMR, MS, elemental analyses and X-ray diffraction. It crystallizes in the monoclinic system, space group P21/n with a=11.541(16), b=8.226(12), c=13.683(19)Å, β=94.872(17)°, V=1294(3)Å3, Z=4 and R=0.0648 for 2198 observed reflections with I>2σ(I). The preliminary biological test shows that the title compound has good activity against Pythium ultimum with inhibitory to be 100%.
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    1. [1]

      Liu X. H, Tan C. X, Weng J. Q. Synthesis, dimeric crystal, and fungicidal activity of 1-(4-methylphenyl)-2-(5-((3,5-dimethyl-1H-pyrazol-1-yl) methyl)-4-phenyl-4H-1,2,4-triazol-3-ylthio)ethanone[J]. Phosphorus Sulfur Silicon Relat. Elem, 2011,186:558-564. doi: 10.1080/10426507.2010.508060

    2. [2]

      Liu X. H, Pan L, Ma Y, Weng J. Q, Tan C. X, Li Y. H, Shi Y. X, Li B. J, Li Z. M, Zhang Y. G. Design, synthesis, biological activities, and 3D-QSAR of new N,N?-diacylhydrazines containing 2-(2,4-dichlorophenoxy)propane moiety[J]. Chem. Biol. Drug Des, 2011,78:689-694. doi: 10.1111/jpp.2011.78.issue-4

    3. [3]

      Yan S. L, Yang M. Y, Sun Z. H, Min L. J, Tan C. X, Weng J. Q, Wu H. K, Liu X. H. Synthesis and antifungal activity of 1,2,3-thiadiazole derivatives containing 1,3,4-thiadiazole moiety[J]. Lett. Drug Des. Discov, 2014,11:940-943. doi: 10.2174/1570180811666140423222141

    4. [4]

      Sun G. X, Shi Y. X, Sun Z. H, Yang M. Y, Wu H. K, Weng J. Q, Tan C. X, Liu X. H, Li B. J, Zhang Y. G. Synthesis and bioactivities of novel 1,3,4-oxadiazole derivatives containing pyridine moiety[J]. Lett. Drug Des. Discov, 2014,11:1119-1123. doi: 10.2174/1570180811666140522002929

    5. [5]

      Gan X. H, Hu D. Y, Li P, Wu J, Chen X. W, Xue W, Song B. A. Design, synthesis, antiviral activity and three-dimensional quantitative structure-activity relationship study of novel 1,4-pentadien-3-one derivatives containing the 1,3,4-oxadiazole moiety[J]. Pest Manag. Sci, 2016,72:534-543. doi: 10.1002/ps.2016.72.issue-3

    6. [6]

      Salar U, Miana G. A, Khan K. M, Naz F, Siddiqui N. I, Taha M, Tauseef S, Khan S, Perveen S. Biology-oriented syntheses (BIOS) of novel santonic-1,3,4-oxadiazole derivatives under microwave-irradiation and their antimicrobial activity[J]. J. Chem. Soc. Pak, 2015,37:1020-1029.

    7. [7]

      Dawood K. M, Gomha S. M. Synthesis and anti-cancer activity of 1,3,4-thiadiazole and 1,3-thiazole derivatives having 1,3,4-oxadiazole moiety[J]. J. Heterocycl. Chem, 2015,52:1400-1405. doi: 10.1002/jhet.v52.5

    8. [8]

      Yang M. Y, Zhai Z. W, Sun Z. H, Yu S. J, Liu X. H, Weng J. Q, Tan C. X, Zhao W. G. A facile one-pot synthesis of novel 1,2,4-triazolo[4,3-a]pyridine derivatives containing the trifluoromethyl moiety using microwave irradiation[J]. J. Chem. Res, 2015,39:521-523. doi: 10.3184/174751915X14400874295745

    9. [9]

      Liu X. H, Tan C. X, Weng J. Q. Phase transfer-catalyzed, one-pot synthesis of some novel N-pyrimidinyl-N?-nicotinyl thiourea derivatives[J]. Phosphorus Sulfur Silicon Relat. Elem, 2011,186:552-557. doi: 10.1080/10426507.2010.508059

    10. [10]

      Liu X. H, Sun Z. H, Yang M. Y, Tan C. X, Weng J. Q, Zhang Y. G, Ma Y. Microwave assistant one pot synthesis, crystal structure, antifungal activities and 3D-QSAR of novel 1,2,4-triazolo[4,3-a]pyridines[J]. Chem. Biol. Drug Des, 2014,84:342-347. doi: 10.1111/cbdd.2014.84.issue-3

    11. [11]

      Zhai Z. W, Shi Y. X, Yang M. Y, Zhao W, Sun Z. H, Weng J. Q, Tan C. X, Liu X. H, Li B. J, Zhang Y. G. Microwave assisted synthesis and antifungal activity of some novel thioethers containing 1,2,4-triazolo[4,3-a]pyridine moiety[J]. Lett. Drug Des. Discov, 2016,13:521-525. doi: 10.2174/157018081306160618181757

    12. [12]

      Shen Z. H, Shi Y. X, Yang M. Y, Sun Z. H, Weng J. Q, Tan C. X, Liu X. H, Li B. J, Zhao W. G. Synthesis, crystal structure, DFT studies and biological activity of a novel schiff base containing triazolo[4,3-a]pyridine moiety[J]. Chin. J. Struct. Chem, 2016,35:457-464.  

    13. [13]

      Zhai Z. W, Shi Y. X, Yang M. Y, Sun Z. H, Weng J. Q, Tan C. X, Liu X. H, Li B. J, Zhang Y. G. Synthesis, crystal structure, DFT studies and antifungal activity of 5-(4-cyclopropyl-5-((3-fluorobenzyl)sulfonyl)-4H-1,2,4-triazol-3-yl)-4-methyl-1,2,3-thiadiazole[J]. Chin. J. Struct. Chem, 2016,35:25-33.

    14. [14]

      Zampieri D, Mamolo M. G, Vio L, Romano M, Skoko N, Baralle M, Pau V, De Logu A. Antimycobacterial activity of new N-1-[1-[1-aryl-3-[4-(1H-imidazol-1-yl)phenyl]-3-oxo]propyl]-pyridine-2-carboxamidrazone derivatives[J]. Bioorg. Med. Chem. Lett, 2016,26:3287-3290. doi: 10.1016/j.bmcl.2016.05.053

    15. [15]

      Kroth H, Sreenivasachary N, Hamel A, Benderitter P, Varisco Y, Giriens V, Paganetti P, Froestl W, Pfeifer A, Muhs A. Synthesis and structure-activity relationship of 2,6-disubstituted pyridine derivatives as inhibitors of beta-amyloid-42 aggregation[J]. Bioorg. Med. Chem. Lett, 2016,26:3330-3335. doi: 10.1016/j.bmcl.2016.05.040

    16. [16]

      Liu X. H, Xu X. Y, Tan C. X, Weng J. Q, Xin J. H, Chen J. Synthesis, crystal structure, herbicidal activities and 3D-QSAR study of some novel 1,2,4-triazolo[4,3-a]pyridine derivatives[J]. Pest Manag. Sci, 2015,71:292-301. doi: 10.1002/ps.2015.71.issue-2

    17. [17]

      Liu X. H, Zhai Z. W, Xu X. Y, Yang M. Y, Sun Z. H, Weng J. Q, Tan C. X, Chen J. Facile and efficient synthesis and biological activity determination of novel 1,2,4-triazolo[4,3-a]pyridin-3(2H)-one derivatives via microwave irradiation[J]. Bioorg. Med. Chem. Lett, 2015,25:5524-5528. doi: 10.1016/j.bmcl.2015.10.064

    18. [18]

      Liu X. H, Zhao W, Shen Z. H, Xing J. H, Yuan J, Yang G, Xu T. M, Peng W. L. Synthesis, nematocidal activity and docking study of novel chiral 1-(3-chloropyridin-2-yl)-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide derivatives[J]. Bioorg. Med. Chem. Lett, 2016,26:3626-3628. doi: 10.1016/j.bmcl.2016.06.004

    19. [19]

      Zhao W, Shen Z. H, Xu T. M, Peng W. L, Liu X. H. Synthesis, nematocidal activity and docking study of novel chiral 1-(3-chloropyridin-2-yl)-3-(difluoromethyl)-1H-pyrazole-4-carboxamide derivatives[J]. J. Heterocycl. Chem, 2016. doi: 10.1002/jhet.2753

    20. [20]

      Liu X.H, Zhao W, Shen Z.H, Xing J.H, Xu T.M, Peng W.L. Synthesis, nematocidal activity and SAR study of novel difluoromethylpyrazole carboxamide derivatives containing flexible alkyl chain moieties[J]. Eur. J. Med. Chem, 2017. doi: 10.1016/j.ejmech.2016.10.017

    21. [21]

      Liu X. H, Wang Q, Sun Z. H, Wedge D. E, Becnel J. J, Estep A. S, Tan C. X, Weng J. Q. Synthesis and insecticidal activity of novel pyrimidine derivatives containing urea pharmacophore against[J]. Aedes aegypti. Pest Manag Sci, 2016. doi: 10.1002/ps.4370

    22. [22]

      Zhao W, Xing J. H, Xu T. M, Peng W. L, Liu X. H. Synthesis and in vivo nematocidal evaluation of novel N-substituted 3-(trifluoromethyl)-1H-pyrazole-4-carboxamide derivatives[J]. Front. Chem. Sci. Eng, 2016. doi: 10.1007/s11705-016-1595-x

    23. [23]

      Zhao W, Shen Z.H, Xu T.M, Peng W.L, Liu X.H. Synthesis and nematocidal activity of novel pyrazole carboxamide derivatives against Meloidogyne incognita[J]. Lett. Drug Des. Discov, 2017,14. doi: 10.2174/1570180813666160930164327

    24. [24]

      Sheldrick, G. M. SHELXS97. Program for Crystal Structure Solution. University of Göttingen, Germany, 1997.

    25. [25]

      Sheldrick, G. M. SHELXL97. Program for Crystal Structure Refinement. University of Göttingen, Germany, 1997.

    26. [26]

      Sheldrick G. M. A short history of SHELX[J]. Acta Crystallogr, 2008,A64:112-122.

    27. [27]

      Wang Q, Zhai Z. W, Sun Z. H, Liu X. H, Tan C. X, Weng J. Q. Synthesis, crystal structure and antifungal activity of 8-chloro-3-((4-chlorobenzyl)thio)[1,2,4]triazolo[4,3-a]pyridine[J]. Chin. J. Struct. Chem, 2016,35:651-655.  

    28. [28]

      Yang M. Y, Zhao W, Liu X. H, Tan C. X, Weng J. Q. Synthesis, crystal structure and antifungal activity of 4-(5-((2,4-dichlorobenzyl)thio)-4-phenyl-4H-1,2,4-triazol-3-yl)pyridine[J]. Chin. J. Struct. Chem, 2015,34:203-207.  

    29. [29]

      Chen M, Yang C. L. Synthesis, crystal structure and biological activity of 5-(2-methylphenyl)-1,3,4-oxadiazol-2(3H)-one derivatives[J]. Chin. J. Struct. Chem, 2015,34:189-196.  

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