Citation: Yue SUN, Zi-Hui YANG, Wen GU. Synthesis, Crystal Structure and Antifungal Activity of New Furan-1, 3, 4-oxadiazole Carboxamide Derivatives[J]. Chinese Journal of Structural Chemistry, ;2022, 41(2): 220209. doi: 10.14102/j.cnki.0254-5861.2011-3232 shu

Synthesis, Crystal Structure and Antifungal Activity of New Furan-1, 3, 4-oxadiazole Carboxamide Derivatives

Jiangsu Provincial Key Lab for the Chemistry and Utilization of Agro-forest Biomass, Jiangsu Key Lab of Biomass-based Green Fuels and Chemicals, Co-inovation Center for Efficient Processing and Utilization of Forest Products, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China

Corresponding author: Wen GU, njguwen@163.com
Received Date: 23 April 2021
Accepted Date: 29 June 2021

Fund Project: the National Natural Science Foundation of China 31770616the Natural Science Foundation for Colleges and Universities in Jiangsu Province 17KJA220002

Figures(3)

A series of novel furan-1, 3, 4-oxadiazole carboxamide derivatives (5a~5e) were designed, synthesized and characterized by spectroscopic methods including HR-MS, ¹H- and ¹³C-NMR. The crystal structure of compound 5a was determined by single-crystal X-ray diffraction. The compound crystallizes in the triclinic system, space group P\begin{document}$ \overline 1 $\end{document} with a = 4.7261(5), b = 10.4672(11), c = 14.5886(13) Å, α = 106.081(4)°, β = 91.043(3)°, γ = 99.456(4)°, Z = 2, V = 682.48(12) Å³, M_r = 348.16, D_c = 1.694 Mg/m³, S = 1.008, μ = 3.025 mm^-1, F(000) = 348, the final R = 0.0775 and wR = 0.2080 for 2774 observed reflections (I > 2σ(I)). There are two kinds of hydrogen bonds (N(3)–H(3A)⋅⋅⋅N(2) and C(8)–H(8A)⋅⋅⋅O(3)) present in its crystal structure. The preliminary antifungal assay showed that compounds 5b and 5c exhibited significant antifungal activities against several plant pathogenic fungi.
- furan-1, 3, 4-oxadiazole carboxamide,
- synthesis,
- crystal structure,
- antifungal activity
1. [1]
  Sparks, T. C.; Lorsbach, B. A. Perspectives on the agrochemical industry and agrochemical discovery. Pest Manag. Sci. 2017, 73, 672–677. doi: 10.1002/ps.4457
2. [2]
  Wang, P. Y.; Wang, M. W.; Zeng, D.; Xiang, M.; Rao, J. R.; Liu, Q. Q.; Liu, L. W.; Wu, Z. B.; Li, Z.; Song, B. A.; Yang, S. Rational optimization and action mechanism of novel imidazole (or imidazolium)-labeled 1, 3, 4-oxadiazole thioethers as promising antibacterial agents against plant bacterial diseases. J. Agric. Food Chem. 2019, 67, 3535−3545. doi: 10.1021/acs.jafc.8b06242
3. [3]
  Dasgin, S.; Gok, Y.; Celepci, D. B.; Taslimi, P.; Izmirli, M.; Aktas, A.; Gulcin, I. Synthesis, characterization, crystal structure and bioactivity properties of the benzimidazole-functionalized PEPPSI type of Pd(II) NHC complexes. J. Mol. Struct. 2021, 1228, 9.
4. [4]
  Mi, Y.; Zhang, J.; Han, X.; Tan, W.; Miao, Q.; Cui, J.; Li, Q.; Guo, Z. Modification of carboxymethyl inulin with heterocyclic compounds: synthesis, characterization, antioxidant and antifungal activities. Int. J. Biol. Macromol. 2021, 181, 572–581. doi: 10.1016/j.ijbiomac.2021.03.109
5. [5]
  Tsai, S. E.; Li, S. M.; Tseng, C. C.; Chung, C. Y.; Zeng, Y. H.; Lin, C. C.; Fuh, M. T.; Yang, L. C.; Yang, Y. C.; Wong, F. F. Chlorotrimethylsilane promoted one-flask heterocyclic synthesis of 1, 2, 4-triazoles from nitrilimines: modeling studies and bioactivity evaluation of LH-21 and Rimonabant analogues. Bioorg. Chem. 2020, 104, 104299. doi: 10.1016/j.bioorg.2020.104299
6. [6]
  El Mansouri, A. E.; Oubella, A.; Mehdi, A.; AitItto, M. Y.; Zahouily, M.; Morjani, H.; Lazrek, H. B. Design, synthesis, biological evaluation and molecular docking of new 1, 3, 4-oxadiazole homonucleosides and their double-headed analogs as antitumor agents. Bioorg. Chem. 2021, 108, 104558. doi: 10.1016/j.bioorg.2020.104558
7. [7]
  Briki, K.; Othman, A. A.; Abbassi, M. S.; Lahrech, M. B. Synthesis, characterization and biological activity of Hg(II), Fe(III) complexes with 1, 3, 4-oxadiazole, 1, 2, 4-triazole derivatives from L-methionine. J. Saudi Chem. Soc. 2020, 24, 1051–1059. doi: 10.1016/j.jscs.2020.11.004
8. [8]
  Li, Y. T.; Yao, W. Q.; Lin, J.; Gao, G. L.; Huang, C.; Wu, Y. Design, synthesis, and biological evaluation of phenyloxadiazole derivatives as potential antifungal agents against phytopathogenic fungi. Mon. Chem. 2021, 152, 121–135. doi: 10.1007/s00706-020-02717-z
9. [9]
  Yang, S.; Tian, X. Y.; Ma, T. Y.; Dai, L.; Ren, C. L.; Mei, J. C.; Liu, X. H.; Tan, C. X. Synthesis and biological activity of benzamides substituted with pyridine-linked 1, 2, 4-oxadiazole. Molecules 2020, 25, 3500. doi: 10.3390/molecules25153500
10. [10]
  Olmez, N. A.; Waseer, F. New potential biologically active compounds: synthesis and characterization of urea and thiourea derivativpes bearing 1, 2, 4-oxadiazole ring. Curr. Org. Synth. 2020, 17, 525–534. doi: 10.2174/1570179417666200417112106
11. [11]
  Szulczyk, D.; Bielenica, A.; Roszkowski, P.; Dobrowolski, M. A.; Olejarz, W.; Kmiecik, S.; Podsiad, M.; Struga, M. Synthetic transition from thiourea-based compounds to tetrazole derivatives: structure and biological evaluation of synthesized new N-(furan-2-ylmethyl)-1H-tetrazol-5-amine derivatives. Molecules 2021, 26, 323. doi: 10.3390/molecules26020323
12. [12]
  Wei, M. X.; Yu, J. Y.; Liu, X. X.; Li, X. Q.; Zhang, M. W.; Yang, P. W.; Yang, J. H. Synthesis of artemisinin-piperazine-furan ether hybrids and evaluation of invitro cytotoxic activity. Eur. J. Med. Chem. 2021, 215, 113295. doi: 10.1016/j.ejmech.2021.113295
13. [13]
  Khalaf, H. S.; Tolan, H. E. M.; El Bayaa, M. N.; Radwan, M. A. A.; El Manawaty, M.; El Sayed, W. A. Synthesis and anticancer activity of new pyridine-thiophene and pyridine-furan hybrid compounds, their sugar hydrazone, and glycosyl derivatives. Russ. J. Gen. Chem. 2020, 90, 1706–1715. doi: 10.1134/S1070363220090182
14. [14]
  Kumar, N.; Gusain, A.; Kumar, J.; Singh, R.; Hota, P. K. Anti-oxidation properties of 2-substituted furan derivatives: a mechanistic study. J. Lumin. 2021, 230, 117725. doi: 10.1016/j.jlumin.2020.117725
15. [15]
  Kanishchev, O. S.; Lavoignat, A.; Picot, S.; Medebielle, M.; Bouillon, J. P. New route to the 5-((arylthio- and heteroarylthio)methylene)-3-(2, 2, 2-trifluoroethyl)-furan-2(5H)-ones-key intermediates in the synthesis of 4-aminoquinoline gamma-lactams as potent antimalarial compounds. Bioorg. Med. Chem. Lett. 2013, 23, 6167–6171. doi: 10.1016/j.bmcl.2013.08.108
16. [16]
  Tighadouini, S.; Radi, S.; Benabbes, R.; Youssoufi, M. H.; Shityakov, S.; El Massaoudi, M.; Garcia, Y. Synthesis, biochemical characterization, and theoretical studies of novel beta-keto-enol pyridine and furan derivatives as potent antifungal agents. Acs Omega. 2020, 5, 17743–17752. doi: 10.1021/acsomega.0c02365
17. [17]
  Zhang, X.; Xu, J.; Muhayimana, S.; Xiong, H.; Liu, X.; Huang, Q. Antifungal effects of 3-(2-pyridyl)methyl-2-(4-chlorphenyl) iminothiazolidine against Sclerotinia sclerotiorum. Pest Manag. Sci. 2020, 76, 2978–2985.
18. [18]
  Tao, P.; Wu, C.; Hao, J.; Gao, Y.; He, X.; Li, J.; Shang, S.; Song, Z.; Song, J. Antifungal application of rosin derivatives from renewable pine resin in crop protection. J. Agric. Food Chem. 2020, 68, 4144–4154. doi: 10.1021/acs.jafc.0c00562
19. [19]
  Zhao, L. X.; Jiang, M. J.; Hu, J. J.; Zou, Y. L.; Cheng, Y.; Ren, T.; Gao, S.; Fu, Y.; Ye, F. Design, synthesis, and herbicidal activity of novel diphenyl ether derivatives containing fast degrading tetrahydrophthalimide. J. Agric. Food Chem. 2020, 68, 3729–3741. doi: 10.1021/acs.jafc.0c00947
20. [20]
  Zhu, S. J.; Xu, S. C.; Jing, W.; Zhao, Z. D.; Jiang, J. X. Synthesis and herbicidal activities of p-menth-3-en-1-amine and its Schiff base derivatives. J. Agric. Food Chem. 2016, 64, 9702–9707. doi: 10.1021/acs.jafc.6b03977
21. [21]
  Zhu, J. K.; Gao, J. M.; Yang, C. J.; Shang, X. F.; Zhao, Z. M.; Lawoe, R. K.; Zhou, R.; Sun, Y.; Yin, X. D.; Liu, Y. Q. Design, synthesis, and antifungal evaluation of neocryptolepine derivatives against phytopathogenic fungi. J. Agric. Food Chem. 2020, 68, 2306–2315. doi: 10.1021/acs.jafc.9b06793
22. [22]
  Yu, B.; Zhou, S.; Cao, L.; Hao, Z.; Yang, D.; Guo, X.; Zhang, N.; Bakulev, V. A.; Fan, Z. Design, synthesis, and evaluation of the antifungal activity of novel pyrazole-thiazole carboxamides as succinate dehydrogenase inhibitors. J. Agric. Food Chem. 2020, 68, 7093–7102. doi: 10.1021/acs.jafc.0c00062
23. [23]
  Pedreira, J. G. B.; Philipp, N.; Mark, K.; Tatu, P.; Benedict, T. B.; Michael, F.; Stefan, K.; Stefan, L.; Eliezer, B. Bioisosteric replacement of arylamide-linked spine residues with N-acylhydrazones and selenophenes as a design strategy to novel dibenzosuberone derivatives as type I 1/2 p38α MAP kinase inhibitors J. Med. Chem. 2020, 63, 7347–7354.
24. [24]
  Yang, Z. H.; Guo, L.; Zhou, C.; Wang, X.; Yu, M.; Min, X.; Yang, K. Synthesis and biological evaluation of nicotinamide derivatives with a diarylamine-modified scaffold as succinate dehydrogenase inhibitors. J. Pestic. Sci. 2020, 45, 1–6.
25. [25]
  Zhang, L.; Li, W.; Xiao, T.; Song, Z.; Csuk, R.; Li, S. K. Design and discovery of novel chiral antifungal amides with 2-(2-oxazolinyl)aniline as a promising pharmacophore. J. Agric. Food Chem. 2018, 66, 8957–8965. doi: 10.1021/acs.jafc.8b02778
1. [1]
  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
2. [2]
  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
3. [3]
  Jia JI , Zhaoyang GUO , Wenni LEI , Jiawei ZHENG , Haorong QIN , Jiahong YAN , Yinling HOU , Xiaoyan XIN , Wenmin WANG . Two dinuclear Gd(Ⅲ)-based complexes constructed by a multidentate diacylhydrazone ligand: Crystal structure, magnetocaloric effect, and biological activity. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 761-772. doi: 10.11862/CJIC.20240344
4. [4]
  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
5. [5]
  Lulu DONG , Jie LIU , Hua YANG , Yupei FU , Hongli LIU , Xiaoli CHEN , Huali CUI , Lin LIU , Jijiang WANG . Synthesis, crystal structure, and fluorescence properties of Cd-based complex with pcu topology. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 809-820. doi: 10.11862/CJIC.20240171
6. [6]
  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
7. [7]
  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
8. [8]
  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
9. [9]
  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
10. [10]
  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
11. [11]
  Hongren RONG , Gexiang GAO , Zhiwei LIU , Ke ZHOU , Lixin SU , Hao HUANG , Wenlong LIU , Qi LIU . High-performance supercapacitor based on 1D cobalt-based coordination polymer. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1183-1195. doi: 10.11862/CJIC.20250034
12. [12]
  Yinling HOU , Jia JI , Hong YU , Xiaoyun BIAN , Xiaofen GUAN , Jing QIU , Shuyi REN , Ming FANG . A rhombic Dy₄-based complex showing remarkable single-molecule magnet behavior. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 605-612. doi: 10.11862/CJIC.20240251
13. [13]
  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
14. [14]
  Xiumei LI , Linlin LI , Bo LIU , Yaru PAN . Syntheses, crystal structures, and characterizations of two cadmium(Ⅱ) coordination polymers. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 613-623. doi: 10.11862/CJIC.20240273
15. [15]
  Yukun CHEN , Kexin FENG , Bolun ZHANG , Wentao SONG , Jianjun ZHANG . Syntheses, crystal structures, and diametrically opposed mechanically-stimulated luminescence response of two Mg(Ⅱ) metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1227-1234. doi: 10.11862/CJIC.20240448
16. [16]
  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
17. [17]
  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
18. [18]
  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
19. [19]
  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
20. [20]
  Shuyan ZHAO . Field-induced Co^Ⅱ single-ion magnet with pentagonal bipyramidal configuration. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1583-1591. doi: 10.11862/CJIC.20240231

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(617)
HTML views(11)

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