Synthesis and Fungicidal Activities of Novel 1,2,3,4-Substituted-Furans Derivatives
American Journal of Heterocyclic Chemistry
Volume 4, Issue 3, September 2018, Pages: 42-48
Received: Nov. 18, 2018;
Accepted: Dec. 4, 2018;
Published: Dec. 17, 2018
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Yanlin Zhang, Department of Environmental Monitoring, Guangdong Vocational College of Environmental Protection Engineering, Foshan, China
Zhihui Zou, School of Chemistry and Chemical Engineering, Guangdong Pharmaceutical University, Guangzhou, China
Hua Cao, School of Chemistry and Chemical Engineering, Guangdong Pharmaceutical University, Guangzhou, China
It is well known that furans derivatives have high biological activities and commercialized furans compounds have extensive applications in life science and medicine field, however, the studies on its potential fungicidal activities are rare and lack of reports. In order to find novel candidate compounds with high fungicidal efficiency, a series of furans derivatives were synthesized and their fungicidal activities were evaluated, which provides information for molecular design and modification of furans compounds with highly effective broad-spectrum fungicidal activities. A series of novel 1,2,3,4-substituted-furans derivatives were synthesized by one-pot method and the structures were confirmed by 1H NMR and 13C NMR. The fungicidal activities were evaluated by the mycelium growth rate method in vitro. Compound c7, c14, c15, c17 and c18 against Fusarium oxysporum had comparable activities with chlorothalonil. Among them, compound c14 and c15 against F. oxysporum with EC50 value of 14.71 mg/L and 14.39 mg/L, respectively, which were superior to that of chlorothalonil. Dimethyl 5-methyl-4-(2-phenylethynyl) furan-2,3-dicarboxylate deserved further development as one kind of novel promising fungicidal agents.
Synthesis and Fungicidal Activities of Novel 1,2,3,4-Substituted-Furans Derivatives, American Journal of Heterocyclic Chemistry.
Vol. 4, No. 3,
2018, pp. 42-48.
R. C. D. Brown, Developments in furan syntheses, Angew. Chem. Int. Ed. 2005, 44, pp. 850–852.
S. F. Kirsch, Syntheses of polysubstituted furans: recent developments, Org. Biomol. Chem. 2006, 4, pp. 2076–2080.
D. Kalaitzakis, M. Triantafyllakis, I. Alexopoulou, et al., One-pot transformation of simple furans into 4-hydroxy-2-cyclopentenones in water, Angew. Chem. Int. Ed. 2014, 53, pp. 13201–13205.
Y. J. Shi, S. L. Wang, H. B. He, et al., Synthesis and bioactivity of novel pyrazole oxime ester derivatives containing furan moiety, Chin. J. Org. Chem. 2015, 35, pp. 1785–1791.
F. Hasegawa, K. Niidome, C. Migihashi, et al., Discovery of furan-2-carbohydrazides as orally active glucagon receptor antagonists, Bioorg. Med. Chem. Lett. 2014, 24, pp. 4266–4270.
J. Q. Huo, L. Y. Ma, Z. Zhang, et al., Synthesis and biological activity of novel N-(3-furan-2-yl-1-phenyl-1H-pyrazol-5-yl) amides derivatives, Chin. Chem. Lett. 2016, 9, pp. 1547–1550.
Kobeissy A A, Hashash J G, Jamali F R, Skoury A M, Haddad R, El-Samad S, Ladki R, Aswad R, Soweid A M, World J Gastroenterol, 2012, 19, 2390–2395.
J. P. Gisbert, L. Gonzalez, X. Calvet, Systematic review and meta-analysis: proton pump inhibitor vs. ranitidine bismuth citrate plus two antibiotics in Helicobacter pylori eradication, Helicobacter, 2005, 10, pp. 157–171.
B. Mahesh, B. Yim, D. Robson, et al., Does furosemide prevents renal dysfunction in high-risk cardiac surgical patients? Result of a double-blinded prospective randomised trial, Eur. J. Cardiothorac. Surg. 2008, 33, pp. 370–376.
B. Meryem, A. W. Noori, E. H. Redouan, et al., Comparison of hypotensive, diuretic and renal effects between cladodes of Opuntia ficus-indica and furosemide, Asian Pac. J. Trop. Med. 2017, 9, pp. 900–906.
Y. Xie, Y. Zhu, H. Zhou, et al., Furazolidone-based triple and quadruple eradication therapy for Helicobacter pylori infection, World J. Gastroenterol. 2014, 32, pp. 11415–11421.
M. Zamani, A. Rahbar, J. Shokri-Shirvani. Resistance of Helicobacter pylori to furazolidone and levofloxacin: A viewpoint, World J. Gastroenterol. 2017, 37, pp. 6920–6922.
M. Vass, K. Hruska, M. Franek, Nitrofuran antibiotics: a review on the application, prohibition and residual analysis, Vet. Med. Czech, 2008, 9, pp. 469–500.
T. Alarcón, P. de la Obra, D. Domingo, et al., In vitro activity of furazolidone and nitrofurantoin in Helicobacter pylori clinical isolates and study of mutation rate. Rev. Esp. Quim. 2005, 18, pp. 313–318.
Rosenthal A, Neter E, Weppner D F, Recovery from Salmonella meningitis after treatment with furaltadone (Altafur), J Pediatr, 1961, 3, pp. 377.
G. J. Liu, R. M. Wilkins, Lethal and anitfeeding effects of carbofuran against the whitebacked planthopper, Chin. J. Rcie Sci. 1992, 3, pp. 119–124.
L. L. Peng, X. Zhang, J. Ma, Synthesis of furan from allenic sulfide derivatives, Sci. China Chem. 2009, 10, pp. 1622–1630.
J. M. Liu, X. Y. Liu, X. S. Qing, et al., I2/K2CO3-promoted ring-opening/cyclization/ rearrangement/aromatization sequence: A powerful strategy for the synthesis of polysubstituted furans, Chin. Chem. Lett. 2017, 2, pp. 458–462.
M. Miao, X. Xu, L. Xu, Copper (I) iodide mediated iodocyclization of cyclopropylideneallenyl ketones: facile and effective synthesis of highly substituted furan derivatives, Eur. J. Org. Chem. 2014, 27, pp. 5896–5900.
C. He, S. Guo, J. Ke, et al., Silver-mediated oxidative C–H/C–H functionalization: a strategy to construct polysubstituted furans, J. Am. Chem. Soc. 2012, 134, pp. 5766–5769.
J. Wu, N. Yoshikai, Modular synthesis of multisubstituted furans through palladium-catalyzed three-component condensation of alkynylbenziodoxoles carboxylic acids, and imines, Angew. Chem. Int. Ed. 2015, 54, pp. 11107–11111.
H. Yu, Z. Ning, Y. Li, J. Gao, Preparation and antimicrobial activity of α-fury lacrylic acid, J. Anhui Agr. Univ., 2006, 3, pp. 351-355.
C. Ma, Y. Ma, T. Li, J. Wang, Structure and activity of secondary metabolites of Endophytic fungus S19 strain in Cephalotaxus fortunei, Guizhou Agr. Sci., 2014, 12, pp. 152-156.