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
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
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
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
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
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
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
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.
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
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
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
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
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
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.
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.
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
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
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
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
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
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
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
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
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
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
Sheldrick, G. M. SHELXS97. Program for Crystal Structure Solution. University of Göttingen, Germany, 1997.
Sheldrick, G. M. SHELXL97. Program for Crystal Structure Refinement. University of Göttingen, Germany, 1997.
Sheldrick G. M. A short history of SHELX[J]. Acta Crystallogr, 2008,A64:112-122.
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.
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.
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.
Yao HUANG , Yingshu WU , Zhichun BAO , Yue HUANG , Shangfeng TANG , Ruixue LIU , Yancheng LIU , Hong LIANG . Copper complexes of anthrahydrazone bearing pyridyl side chain: Synthesis, crystal structure, anticancer activity, and DNA binding. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 213-224. doi: 10.11862/CJIC.20240359
Chao LIU , Jiang WU , Zhaolei JIN . Synthesis, crystal structures, and antibacterial activities of two zinc(Ⅱ) complexes bearing 5-phenyl-1H-pyrazole group. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1986-1994. doi: 10.11862/CJIC.20240153
Xiaoxia WANG , Ya'nan GUO , Feng SU , Chun HAN , Long SUN . Synthesis, structure, and electrocatalytic oxygen reduction reaction properties of metal antimony-based chalcogenide clusters. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1201-1208. doi: 10.11862/CJIC.20230478
Xiaoling WANG , Hongwu ZHANG , Daofu LIU . Synthesis, structure, and magnetic property of a cobalt(Ⅱ) complex based on pyridyl-substituted imino nitroxide radical. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 407-412. doi: 10.11862/CJIC.20240214
Kaimin WANG , Xiong GU , Na DENG , Hongmei YU , Yanqin YE , Yulu MA . Synthesis, structure, fluorescence properties, and Hirshfeld surface analysis of three Zn(Ⅱ)/Cu(Ⅱ) complexes based on 5-(dimethylamino) isophthalic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1397-1408. doi: 10.11862/CJIC.20240009
Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
Ruikui YAN , Xiaoli CHEN , Miao CAI , Jing REN , Huali CUI , Hua YANG , Jijiang WANG . Design, synthesis, and fluorescence sensing performance of highly sensitive and multi-response lanthanide metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 834-848. doi: 10.11862/CJIC.20230301
Lu LIU , Huijie WANG , Haitong WANG , Ying LI . Crystal structure of a two-dimensional Cd(Ⅱ) complex and its fluorescence recognition of p-nitrophenol, tetracycline, 2, 6-dichloro-4-nitroaniline. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1180-1188. doi: 10.11862/CJIC.20230489
Xiumei LI , Yanju HUANG , Bo LIU , Yaru PAN . Syntheses, crystal structures, and quantum chemistry calculation of two Ni(Ⅱ) coordination polymers. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 2031-2039. doi: 10.11862/CJIC.20240109
Yan XU , Suzhi LI , Yan LI , Lushun FENG , Wentao SUN , Xinxing LI . Structure variation of cadmium naphthalene-diphosphonates with the changing rigidity of N-donor auxiliary ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 395-406. doi: 10.11862/CJIC.20240226
Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
Huan ZHANG , Jijiang WANG , Guang FAN , Long TANG , Erlin YUE , Chao BAI , Xiao WANG , Yuqi ZHANG . A highly stable cadmium(Ⅱ) metal-organic framework for detecting tetracycline and p-nitrophenol. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 646-654. doi: 10.11862/CJIC.20230291
Meirong HAN , Xiaoyang WEI , Sisi FENG , Yuting BAI . A zinc-based metal-organic framework for fluorescence detection of trace Cu2+. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1603-1614. doi: 10.11862/CJIC.20240150
Shuyan ZHAO . Field-induced CoⅡ single-ion magnet with pentagonal bipyramidal configuration. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1583-1591. doi: 10.11862/CJIC.20240231
Xiaofen GUAN , Yating LIU , Jia LI , Yiwen HU , Haiyuan DING , Yuanjing SHI , Zhiqiang WANG , Wenmin WANG . Synthesis, crystal structure, and DNA-binding of binuclear lanthanide complexes based on a multidentate Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2486-2496. doi: 10.11862/CJIC.20240122
Yun-Feng Liu , Hui-Fang Du , Ya-Hui Zhang , Zhi-Qin Liu , Xiao-Qian Qi , Du-Qiang Luo , Fei Cao . Chaeglobol A, an unusual octocyclic sterol with antifungal activity from the marine-derived fungus Chaetomium globosum HBU-45. Chinese Chemical Letters, 2025, 36(3): 109858-. doi: 10.1016/j.cclet.2024.109858
Xiaowei TANG , Shiquan XIAO , Jingwen SUN , Yu ZHU , Xiaoting CHEN , Haiyan ZHANG . A zinc complex for the detection of anthrax biomarker. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1850-1860. doi: 10.11862/CJIC.20240173
Teng-Yu Huang , Junliang Sun , De-Xian Wang , Qi-Qiang Wang . Recent progress in chiral zeolites: Structure, synthesis, characterization and applications. Chinese Chemical Letters, 2024, 35(12): 109758-. doi: 10.1016/j.cclet.2024.109758
Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb2 complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357