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

a.
School of Chemistry and Chemical Engineering, Yancheng Institute of Technology, Yancheng, Jiangsu 224051, China
b.
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China
c.
Institute of Vegetables and Flowers, Chinese Academy of Agricultural Sciences, Beijing 100014, China

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%.
- oxadiazole compound,
- synthesis,
- crystal structure,
- antifungal activity
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.
1. [1]
  WANG Qiao , ZHAI Zhi-Wen , SUN Zhao-Hui , LIU Xing-Hai , TAN Cheng-Xia , WENG Jian-Quan . Synthesis, Crystal Structure and Antifungal Activity of 8-Chloro-3-((4-chlorobenzyl)-thio)[1,2,4]triazolo[4,3-a]pyridine. Chinese Journal of Structural Chemistry, 2016, 35(4): 651-655. doi: 10.14102/j.cnki.0254-5861.2011-1022
2. [2]
  ZHAI Zhi-Wen , SHI Yan-Xia , YANG Ming-Yan , SUN Zhao-Hui , WENG Jian-Quan , TAN Cheng-Xia , LIU Xing-Hai , LI Bao-Ju , ZHANG Yong-Gang . 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. Chinese Journal of Structural Chemistry, 2016, 35(1): 25-33. doi: 10.14102/j.cnki.0254-5861.2011-0821
3. [3]
  XU Ying-Shu , SHI Da-Bin . Synthesis, Crystal Structure and Antifungal Activities of 3-Methyl-1-(4-methylphenyl)-4-(N-4-trifluoromethylphenyl)-aminomethyl-5-(4-methoxyphenylthio)-1H-pyrazole. Chinese Journal of Structural Chemistry, 2014, 33(1): 37-42.
4. [4]
  SHEN Zhong-Hua , SHI Yan-Xia , YANG Ming-Yan , SUN Zhao-Hui , WENG Jian-Quan , TAN Cheng-Xia , LIU Xing-Hai , LI Bao-Ju , ZHAO Wei-Guang . Synthesis, Crystal Structure, DFT Studies and Biological Activity of a Novel Schiff Base Containing Triazolo[4,3-a]pyridine Moiety. Chinese Journal of Structural Chemistry, 2016, 35(3): 457-464. doi: 10.14102/j.cnki.0254-5861.2011-0913
5. [5]
  SUN Guo-Xiang , SHI Yan-Xia , ZHAI Zhi-Wen , YANG Ming-Yan , WENG Jian-Quan , TAN Cheng-Xia , LIU Xing-Haib , LI Bao-Ju . Synthesis, Crystal Structure and Biological Activity of (E)-3-Chloro-2-(2-(2-methylbenzylidene)-hydrazinyl)pyridine. Chinese Journal of Structural Chemistry, 2016, 35(4): 640-644. doi: 10.14102/j.cnki.0254-5861.2011-0991
6. [6]
  Yue SUN , Zi-Hui YANG , Wen GU . Synthesis, Crystal Structure and Antifungal Activity of New Furan-1, 3, 4-oxadiazole Carboxamide Derivatives. Chinese Journal of Structural Chemistry, 2022, 41(2): 2202098-2202104. doi: 10.14102/j.cnki.0254-5861.2011-3232
7. [7]
  Jin-Xia MU , Chen-Sheng YU , Li-Jing MIN , Xing-Hai LIU . Synthesis, Crystal Structure, Antifungal Activity and Computational Study on 4-(((8-Chloro-3-oxo-[1,2,4]-triazolo[4,3-a]pyridin-2(3H)-yl)thio)methyl)benzonitrile. Chinese Journal of Structural Chemistry, 2021, 40(4): 424-430. doi: 10.14102/j.cnki.0254-5861.2011-2937
8. [8]
  CHEN Hong , XU Wei , XU Fang , HE Xue-Lan , YUAN Mu . Synthesis, Crystal Structure and Cytotoxic Activity of a New NAN-190 Analogue. Chinese Journal of Structural Chemistry, 2014, 33(12): 1773-1778. doi: 10.14102/j.cnki.0254-5861.2011-0369
9. [9]
  YU Yun , HE Jia-Xin , HU Hui-Ling , LIN Zhi-Lan , GAO Yuan . Efficient Synthesis, Crystal Structure and Antibacterial Activity of Two Novel 1,3-Oxazin Derivatives. Chinese Journal of Structural Chemistry, 2014, 33(3): 441-447.
10. [10]
  ZHANG Jing-Yi , ZHONG Han-Yu , SHI Guo-Bing . Synthesis, Crystal Structure and Antiproliferative Activity of Ethyl 1-(Phenylcarbamoyl)-2-3,4,5-trimethoxyphenyl)cyclopropanecarboxylae. Chinese Journal of Structural Chemistry, 2014, 33(6): 876-880.
11. [11]
  CAI Zhi-Qiang , MA Wei-Ying , LIU Ju , HU Zhi-Quan , HOU Ling , WANG Jian-Ya . Synthesis, Crystal Structure and Biological Activity of a New 4,5-Diaryl-1H-imidazole Derivative. Chinese Journal of Structural Chemistry, 2014, 33(9): 1383-1387.
12. [12]
  ZHU Xiao-Ming , KUANG Dai-Zhi , FENG Yong-Lan , ZHANG Fu-Xing , YU Jiang-Xi , JIANG Wu-Jiu , ZHANG Zhi-Jian . Synthesis, Crystal Structure, Thermal Stability and Anti-tumor Activity In Vitro of Bis(tricyclohexyltin) Pimelicarboxylate. Chinese Journal of Structural Chemistry, 2015, 34(11): 1652-1658. doi: 10.14102/j.cnki.0254-5861.2011-0779
13. [13]
  MAO Wu-Tao , ZONG Guang-Ning , FAN Zhi-Jin , LI Feng-Yun , SONG Hai-Bin , LI Juan-Juan , Kalinina A. Tatiana , Khazhieva Inna , Lugovik Ksenia , Morzherin Yu. Yury , Belskaya P. Nataliya . Synthesis, Crystal Structure and Biological Activity of N-cyanosulfoximine Derivative Containing 1,2,3-Thiadiazole. Chinese Journal of Structural Chemistry, 2015, 34(9): 1428-1433. doi: 10.14102/j.cnki.0254-5861.2011-0665
14. [14]
  GUO Rui , OU Zhong-Ping , YE Li-Na , HUANG Wen-Hao , XUE Zhao-Li , TANG Ji-Jun , FANG Yuan-Yuan . Cobalt Triarylcorroles with Sterically Hindered Haloginated Phenyl Rings: Synthesis, Crystal Structure and Catalytic Activity for Electroreduction of Dioxygen. Chinese Journal of Structural Chemistry, 2016, 35(11): 1754-1763. doi: 10.14102/j.cnki.0254-5861.2011-1156
15. [15]
  YANG Ming-Yan , ZHAO Wen , LIU Xing-Hai , TAN Cheng-Xia , WENG Jian-Quan . Synthesis, Crystal Structure and Antifungal Activity of 4-(5-((2,4-Dichlorobenzyl)thio)-4-phenyl-4H-1,2,4-triazol-3-yl)pyridine. Chinese Journal of Structural Chemistry, 2015, 34(2): 203-207. doi: 10.14102/j.cnki.0254-5861.2011-0481
16. [16]
  TAI Xi-Shi , WANG Xin , YOU Hai-Ying . Synthesis, Crystal Structure and Antitumor Activity of a New Zn(II) Complex Based on N-Acetyl-L-phenylalanine and 1,10-Phenanthroline. Chinese Journal of Structural Chemistry, 2016, 35(4): 586-590. doi: 10.14102/j.cnki.0254-5861.2011-0910
17. [17]
  Ju Tao LIU , Xiao Hong WANG , Jing Fu LIU . Synthesis and Crystal Structure of a Novel Compound of (C₂N₂H₈O₂) H₆V₁₀O₂₈. Chinese Chemical Letters, 2004, 15(7): 859-862.
18. [18]
  SHI Xiu-Dong , GE Bing-Chen , XU Jiang-Ping , ZHOU Zhong-Zhen . Synthesis, Crystal Structure and Antitumor Activity of 6-Chloro-1-((6-chloropyridin-3-yl)methyl)-3-phenyl-1H-benzofuro[3,2-c]pyrazole. Chinese Journal of Structural Chemistry, 2016, 35(1): 34-38. doi: 10.14102/j.cnki.0254-5861.2011-0857
19. [19]
  YE Jiao , SUN Xiao-Xiao , QIU Shen-Yi , HU Ai-Xi . Synthesis, Crystal Structure and Fungicidal Activity of N-(4-tert-buty)-5-(1,2,4-triazol-1-yl)thiazol-2-yl)propionamide. Chinese Journal of Structural Chemistry, 2014, 33(3): 429-433.
20. [20]
  LUO Zai-Gang , MA Chao , WU Li-Mei , YUAN Meng-Hong , XU Chuan-Hao , HU Jing-Song , XU Xue-Mei . Synthesis, Crystal Structure and Biological Activity of 25,27-Di(α,γ-diketo-p-methylphenylbutoxy)-26,28-dihydroxy p-tert-butylcalix[4]arene. Chinese Journal of Structural Chemistry, 2014, 33(6): 865-870.

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(5875)
HTML views(192)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142