Synthesis, Crystal Structure and Antifungal Activity of 2-((2-fluorobenzyl)thio)-5-(pyridin-4-yl)-1,3,4-oxadiazole
孙国香;石延霞;翟志文;孙召慧;翁建全;谭成侠;刘幸海;李宝聚
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)
Synthesis, Crystal Structure and Antifungal Activity of 2-((2-fluorobenzyl)thio)-5-(pyridin-4-yl)-1,3,4-oxadiazole
SUN Guo-Xiang;SHI Yan-Xia;ZHAI Zhi-Wen;SUN Zhao-Hui;WENG Jian-Quan;TAN Cheng-Xia;LIU Xing-Hai;LI Bao-Ju
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)
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)º, 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%.
Abstract: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)º, 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%.
This work was funded by the Natural Science Foundation of Zhejiang Province (No. LY16C140007) and the program of Science and Technology of Jiangsu Province (BY2014108-14)
通讯作者:
xhliu@zjut.edu.cn
E-mail: xhliu@zjut.edu.cn
引用本文:
孙国香;石延霞;翟志文;孙召慧;翁建全;谭成侠;刘幸海;李宝聚. Synthesis, Crystal Structure and Antifungal Activity of 2-((2-fluorobenzyl)thio)-5-(pyridin-4-yl)-1,3,4-oxadiazole[J]. 结构化学, 2016, 35(12): 1855-1859.
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. CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2016, 35(12): 1855-1859.
REFERENCES
(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. Phosphorus Sulfur Silicon Relat. Elem. 2011, 186, 558564.
(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. Chem. Biol. Drug Des. 2011, 78, 689694.
(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. Lett. Drug Des. Discov. 2014, 11, 940943.
(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. Lett. Drug Des. Discov. 2014, 11, 11191123.
(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. Pest Manag. Sci. 2016, 72, 534543.
(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. Chem. Soc. Pak. 2015, 37, 10201029.
(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. Heterocycl. Chem. 2015, 52, 14001405.
(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. Chem. Res. 2015, 39, 521523.
(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. Phosphorus Sulfur Silicon Relat. Elem. 2011, 186, 552557.
(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. Chem. Biol. Drug Des. 2014, 84, 342347.
(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. Lett. Drug Des. Discov. 2016, 13, 521525.
(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. Chin. J. Struct. Chem. 2016, 35, 457464.
(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. Chin. J. Struct. Chem. 2016, 35, 2533.
(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. Bioorg. Med. Chem. Lett. 2016, 26, 32873290.
(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. Bioorg. Med. Chem. Lett. 2016, 26, 33303335.
(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. Pest Manag. Sci. 2015, 71, 292301.
(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. Bioorg. Med. Chem. Lett. 2015, 25, 55245528.
(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. Bioorg. Med. Chem. Lett. 2016, 26, 3626–3628.
(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. Heterocycl. Chem. 2016, doi: 10.1002/jhet.2753.
(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. Eur. J. Med. Chem. 2017, doi:10.1016/j.ejmech.2016.10.017.
(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. Aedes aegypti. Pest Manag Sci. 2016, doi: 10.1002/ps.4370.
(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. Front. Chem. Sci. Eng. 2016, doi: 10.1007/s11705-016-1595-x.
(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. Lett. Drug Des. Discov. 2017, 14, doi:10.2174/1570180813666160930164327.
(24) Sheldrick, G. M. SHELXS97. Program for Crystal Structure Solution. University of Göttingen, Germany 1997.
(25) Sheldrick, G. M. SHELXL97. Program for Crystal Structure Refinement. University of Göttingen, Germany 1997.
(26) Sheldrick, G. M. A short history of SHELX. Acta Crystallogr. 2008, A64, 112122.
(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. Chin. J. Struct. Chem. 2016, 35, 651655.
(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. Chin. J. Struct. Chem. 2015, 34, 203207.
(29) Chen, M.; Yang, C. L. Synthesis, crystal structure and biological activity of 5-(2-methylphenyl)-1,3,4-oxadiazol-2(3H)-one derivatives. Chin. J. Struct. Chem. 2015, 34, 189196.