Design, Synthesis, Antiviral Bioactivity, and Mechanism of the Ferulic Acid Ester-Containing Sulfonamide Moiety

Overview

Journal ACS Omega

Publisher American Chemical Society

Specialty Chemistry

Date 2020 Aug 18

PMID 32803067

Citations 13

Authors

Xiaoli Ren

Xiangyang Li

Limin Yin

Donghao Jiang

Deyu Hu

Affiliations

Soon will be listed here.

Abstract

Tobacco mosaic virus (TMV) has caused huge economic losses to tobacco, pepper, cucumber, and ornamental crops all over the world. However, few effective antiviral agents were developed and applied to control such plant disease. It is challenging to find an anti-TMV agent which is highly effective, less toxic, and environmentally friendly. In this work, a series of ferulic acid ester-containing sulfonamide moieties were designed and synthesized, and the antiviral activities of these compounds against TMV were evaluated. The anti-TMV biological activity test showed that the target compounds showed excellent anti-TMV activity and . In particular, compound has excellent anti-TMV activity at 500 μg/mL, which is higher than that of the control drug ribavirin. The preliminary mechanism research results showed that compound can obviously destroy the morphology of the virions to show excellent activity. The results show that the ferulic acid ester-containing sulfonamide moiety deserves further research and development.

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References

Bassetto M, Leyssen P, Neyts J, Yerukhimovich M, Frick D, Courtney-Smith M . In silico identification, design and synthesis of novel piperazine-based antiviral agents targeting the hepatitis C virus helicase. Eur J Med Chem. 2016; 125:1115-1131. DOI: 10.1016/j.ejmech.2016.10.043. View

Wu Z, Zhang J, Chen J, Pan J, Zhao L, Liu D . Design, synthesis, antiviral bioactivity and three-dimensional quantitative structure-activity relationship study of novel ferulic acid ester derivatives containing quinazoline moiety. Pest Manag Sci. 2017; 73(10):2079-2089. DOI: 10.1002/ps.4579. View

Guo W, Yan H, Ren X, Tang R, Sun Y, Wang Y . Berberine induces resistance against tobacco mosaic virus in tobacco. Pest Manag Sci. 2019; 76(5):1804-1813. DOI: 10.1002/ps.5709. View

Bungard C, Williams P, Schulz J, Wiscount C, Holloway M, Loughran H . Design and Synthesis of Piperazine Sulfonamide Cores Leading to Highly Potent HIV-1 Protease Inhibitors. ACS Med Chem Lett. 2017; 8(12):1292-1297. PMC: 5733263. DOI: 10.1021/acsmedchemlett.7b00386. View

Wu M, Wang Z, Meng C, Wang K, Hu Y, Wang L . Discovery and SARs of trans-3-aryl acrylic acids and their analogs as novel anti-tobacco mosaic virus (TMV) agents. PLoS One. 2013; 8(2):e56475. PMC: 3572066. DOI: 10.1371/journal.pone.0056475. View

Huang G, Cui C, Wang Z, Li Y, Xiong L, Wang L . Synthesis and characteristics of (Hydrogenated) ferulic acid derivatives as potential antiviral agents with insecticidal activity. Chem Cent J. 2013; 7(1):33. PMC: 3599306. DOI: 10.1186/1752-153X-7-33. View

Wang Z, Xie D, Gan X, Zeng S, Zhang A, Yin L . Synthesis, antiviral activity, and molecular docking study of trans-ferulic acid derivatives containing acylhydrazone moiety. Bioorg Med Chem Lett. 2017; 27(17):4096-4100. DOI: 10.1016/j.bmcl.2017.07.038. View

Han B, Park C, Takasuka N, Naito A, Sekine K, Nomura E . A ferulic acid derivative, ethyl 3-(4'-geranyloxy-3-methoxyphenyl)-2-propenoate, as a new candidate chemopreventive agent for colon carcinogenesis in the rat. Jpn J Cancer Res. 2001; 92(4):404-9. PMC: 5926721. DOI: 10.1111/j.1349-7006.2001.tb01109.x. View

Ji X, Wang Z, Dong J, Liu Y, Lu A, Wang Q . Discovery of Topsentin Alkaloids and Their Derivatives as Novel Antiviral and Anti-phytopathogenic Fungus Agents. J Agric Food Chem. 2016; 64(48):9143-9151. DOI: 10.1021/acs.jafc.6b04020. View

10.

Qian X, Lee P, Cao S . China: forward to the green pesticides via a basic research program. J Agric Food Chem. 2010; 58(5):2613-23. DOI: 10.1021/jf904098w. View

11.

Lu A, Wang Z, Zhou Z, Chen J, Wang Q . Application of "hydrogen bonding interaction" in new drug development: design, synthesis, antiviral activity, and SARs of thiourea derivatives. J Agric Food Chem. 2015; 63(5):1378-84. DOI: 10.1021/jf505355r. View

12.

Yin L, Gan X, Shi J, Zan N, Zhang A, Ren X . Induced Resistance Mechanism of Novel Curcumin Analogs Bearing a Quinazoline Moiety to Plant Virus. Int J Mol Sci. 2018; 19(12). PMC: 6321402. DOI: 10.3390/ijms19124065. View

13.

Long C, Li P, Chen M, Dong L, Hu D, Song B . Synthesis, anti-tobacco mosaic virus and cucumber mosaic virus activity, and 3D-QSAR study of novel 1,4-pentadien-3-one derivatives containing 4-thioquinazoline moiety. Eur J Med Chem. 2015; 102:639-47. DOI: 10.1016/j.ejmech.2015.08.029. View

14.

Seiber J . Sustainability and agricultural and food chemistry. J Agric Food Chem. 2011; 59(1):1-21. DOI: 10.1021/jf1046078. View

15.

Ou L, Kong L, Zhang X, Niwa M . Oxidation of ferulic acid by Momordica charantia peroxidase and related anti-inflammation activity changes. Biol Pharm Bull. 2003; 26(11):1511-6. DOI: 10.1248/bpb.26.1511. View

16.

Wang Y, Xu F, Luo D, Guo S, He F, Dai A . Synthesis of Anthranilic Diamide Derivatives Containing Moieties of Trifluoromethylpyridine and Hydrazone as Potential Anti-Viral Agents for Plants. J Agric Food Chem. 2019; 67(48):13344-13352. DOI: 10.1021/acs.jafc.9b05441. View

17.

He F, Shi J, Wang Y, Wang S, Chen J, Gan X . Synthesis, Antiviral Activity, and Mechanisms of Purine Nucleoside Derivatives Containing a Sulfonamide Moiety. J Agric Food Chem. 2019; 67(31):8459-8467. DOI: 10.1021/acs.jafc.9b02681. View

18.

Wang Z, Wang L, Ma S, Liu Y, Wang L, Wang Q . Design, synthesis, antiviral activity, and SARs of 14-aminophenanthroindolizidines. J Agric Food Chem. 2012; 60(23):5825-31. DOI: 10.1021/jf3013376. View

19.

Basanagouda M, Shivashankar K, Kulkarni M, Rasal V, Patel H, Mutha S . Synthesis and antimicrobial studies on novel sulfonamides containing 4-azidomethyl coumarin. Eur J Med Chem. 2010; 45(3):1151-7. DOI: 10.1016/j.ejmech.2009.12.022. View

20.

Kim H, Park J, Lee K, Lee D, Kwak J, Kim Y . Ferulic acid protects against carbon tetrachloride-induced liver injury in mice. Toxicology. 2011; 282(3):104-11. DOI: 10.1016/j.tox.2011.01.017. View