Synthesis and Fungicidal Activities of Novel 1,2,3,4-Substituted-Furans Derivatives

Yanlin Zhang; Zhihui Zou; Hua Cao

doi:doi:10.11648/j.ajhc.20180403.11

| Peer-Reviewed

Synthesis and Fungicidal Activities of Novel 1,2,3,4-Substituted-Furans Derivatives

Yanlin Zhang, Zhihui Zou, Hua Cao

Published in American Journal of Heterocyclic Chemistry (Volume 4, Issue 3)

Received: 18 November 2018 Accepted: 4 December 2018 Published: 17 December 2018

Views: Downloads:

Download PDF

Share This Article

Twitter
Linked In
Facebook

Abstract

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.

Published in	American Journal of Heterocyclic Chemistry (Volume 4, Issue 3)
DOI	10.11648/j.ajhc.20180403.11
Page(s)	42-48
Creative Commons	This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.
Copyright	Copyright © The Author(s), 2018. Published by Science Publishing Group

Keywords

Furans Derivatives, Fungicidal Activities, Nano-Cu₂O-Catalyzed Synthesis

References

[1]	R. C. D. Brown, Developments in furan syntheses, Angew. Chem. Int. Ed. 2005, 44, pp. 850–852.
[2]	S. F. Kirsch, Syntheses of polysubstituted furans: recent developments, Org. Biomol. Chem. 2006, 4, pp. 2076–2080.
[3]	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.
[4]	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.
[5]	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.
[6]	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.
[7]	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.
[8]	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.
[9]	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.
[10]	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.
[11]	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.
[12]	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.
[13]	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.
[14]	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.
[15]	Rosenthal A, Neter E, Weppner D F, Recovery from Salmonella meningitis after treatment with furaltadone (Altafur), J Pediatr, 1961, 3, pp. 377.
[16]	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.
[17]	L. L. Peng, X. Zhang, J. Ma, Synthesis of furan from allenic sulfide derivatives, Sci. China Chem. 2009, 10, pp. 1622–1630.
[18]	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.
[19]	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.
[20]	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.
[21]	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.
[22]	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.
[23]	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.

Cite This Article

Plain Text BibTeX RIS

APA Style

Yanlin Zhang, Zhihui Zou, Hua Cao. (2018). Synthesis and Fungicidal Activities of Novel 1,2,3,4-Substituted-Furans Derivatives. American Journal of Heterocyclic Chemistry, 4(3), 42-48. https://doi.org/10.11648/j.ajhc.20180403.11

Copy | Download

ACS Style

Yanlin Zhang; Zhihui Zou; Hua Cao. Synthesis and Fungicidal Activities of Novel 1,2,3,4-Substituted-Furans Derivatives. Am. J. Heterocycl. Chem. 2018, 4(3), 42-48. doi: 10.11648/j.ajhc.20180403.11

Copy | Download

AMA Style

Yanlin Zhang, Zhihui Zou, Hua Cao. Synthesis and Fungicidal Activities of Novel 1,2,3,4-Substituted-Furans Derivatives. Am J Heterocycl Chem. 2018;4(3):42-48. doi: 10.11648/j.ajhc.20180403.11

Copy | Download

@article{10.11648/j.ajhc.20180403.11,
  author = {Yanlin Zhang and Zhihui Zou and Hua Cao},
  title = {Synthesis and Fungicidal Activities of Novel 1,2,3,4-Substituted-Furans Derivatives},
  journal = {American Journal of Heterocyclic Chemistry},
  volume = {4},
  number = {3},
  pages = {42-48},
  doi = {10.11648/j.ajhc.20180403.11},
  url = {https://doi.org/10.11648/j.ajhc.20180403.11},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajhc.20180403.11},
  abstract = {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.},
 year = {2018}
}

Copy | Download

TY  - JOUR
T1  - Synthesis and Fungicidal Activities of Novel 1,2,3,4-Substituted-Furans Derivatives
AU  - Yanlin Zhang
AU  - Zhihui Zou
AU  - Hua Cao
Y1  - 2018/12/17
PY  - 2018
N1  - https://doi.org/10.11648/j.ajhc.20180403.11
DO  - 10.11648/j.ajhc.20180403.11
T2  - American Journal of Heterocyclic Chemistry
JF  - American Journal of Heterocyclic Chemistry
JO  - American Journal of Heterocyclic Chemistry
SP  - 42
EP  - 48
PB  - Science Publishing Group
SN  - 2575-5722
UR  - https://doi.org/10.11648/j.ajhc.20180403.11
AB  - 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.
VL  - 4
IS  - 3
ER  -

Copy | Download

Author Information

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

Download PDF

Sections

Plain Text BibTeX RIS

APA Style

Yanlin Zhang, Zhihui Zou, Hua Cao. (2018). Synthesis and Fungicidal Activities of Novel 1,2,3,4-Substituted-Furans Derivatives. American Journal of Heterocyclic Chemistry, 4(3), 42-48. https://doi.org/10.11648/j.ajhc.20180403.11

Copy | Download

ACS Style

Yanlin Zhang; Zhihui Zou; Hua Cao. Synthesis and Fungicidal Activities of Novel 1,2,3,4-Substituted-Furans Derivatives. Am. J. Heterocycl. Chem. 2018, 4(3), 42-48. doi: 10.11648/j.ajhc.20180403.11

Copy | Download

AMA Style

Yanlin Zhang, Zhihui Zou, Hua Cao. Synthesis and Fungicidal Activities of Novel 1,2,3,4-Substituted-Furans Derivatives. Am J Heterocycl Chem. 2018;4(3):42-48. doi: 10.11648/j.ajhc.20180403.11

Copy | Download

@article{10.11648/j.ajhc.20180403.11,
  author = {Yanlin Zhang and Zhihui Zou and Hua Cao},
  title = {Synthesis and Fungicidal Activities of Novel 1,2,3,4-Substituted-Furans Derivatives},
  journal = {American Journal of Heterocyclic Chemistry},
  volume = {4},
  number = {3},
  pages = {42-48},
  doi = {10.11648/j.ajhc.20180403.11},
  url = {https://doi.org/10.11648/j.ajhc.20180403.11},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajhc.20180403.11},
  abstract = {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.},
 year = {2018}
}

Copy | Download

TY  - JOUR
T1  - Synthesis and Fungicidal Activities of Novel 1,2,3,4-Substituted-Furans Derivatives
AU  - Yanlin Zhang
AU  - Zhihui Zou
AU  - Hua Cao
Y1  - 2018/12/17
PY  - 2018
N1  - https://doi.org/10.11648/j.ajhc.20180403.11
DO  - 10.11648/j.ajhc.20180403.11
T2  - American Journal of Heterocyclic Chemistry
JF  - American Journal of Heterocyclic Chemistry
JO  - American Journal of Heterocyclic Chemistry
SP  - 42
EP  - 48
PB  - Science Publishing Group
SN  - 2575-5722
UR  - https://doi.org/10.11648/j.ajhc.20180403.11
AB  - 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.
VL  - 4
IS  - 3
ER  -

Copy | Download