Synthesis, antibacterial, and antiviral activities of novel penta-1,4-dien-3-one derivatives containing a benzotriazin-4(3H)-one moiety
- 31 Downloads
A series of penta-1,4-dien-3-one containing a benzotriazin-4(3H)-one moiety were prepared and evaluated for their antibacterial and antiviral activities. Bioassays indicated that some compounds exhibited good antibacterial and antiviral activities. Among them, the EC50 values of compound 6d against Xanthomonas axonopodis pv. citri and compound 6l against Ralstonia solanacearum were, respectively, 22.45 and 34.77 μg/mL, which were better than that of thiodiazole copper (51.35 and 87.26 μg/mL, respectively). Meanwhile, some title compounds were found to show remarkable antiviral activities against tobacco mosaic virus (TMV). These results indicated that penta-1,4-dien-3-one derivatives containing benzotriazin-4(3H)-one moiety could play significant roles in searching for novel agrochemicals.
KeywordsPenta-1,4-dien-3-one Antiviral Antibacterial Benzotriazin-4(3H)-one
This research was supported by the National Key Research and Development Program of China (No. 2017YFD0200506), the National Nature Science Foundation of China (No. 21462012), the Special Fund for Outstanding Scientific and Technological Candidates of Guizhou Province (No. 201535), and the Innovation Fund for Graduate Student of Guizhou University (No. 2017059).
- Baldwin PR, Reeves AZ, Powell KR, Napier RJ, Swimm AI, Sun A, Giesler K, Bommarius B, Shinnick TM, Snyder JP, Liotta DC, Kalman D (2015) Monocarbonyl analogs of curcumin inhibit growth of antibiotic sensitive and resistant strains of Mycobacterium tuberculosis. Eur J Med Chem 92:693–699. https://doi.org/10.1016/j.ejmech.2015.01.020 CrossRefGoogle Scholar
- Gan XH, Hu DY, Li P, Wu J, Chen XW, Xue W, Song BA (2016) 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. Pest Manag Sci 72:534–543. https://doi.org/10.1002/ps.4018 CrossRefGoogle Scholar
- Liu ZG, Tang LG, Zou P, Zhang YL, Wang Z, Fang QL, Jiang LL, Chen GZ, Xu Z, Zhang HJ, Liang G (2014) Synthesis and biological evaluation of allylated and prenylated mono-carbonyl analogs of curcumin as anti-inflammatory agents. Eur J Med Chem 74:671–682. https://doi.org/10.1016/j.ejmech.2013.10.061 CrossRefGoogle Scholar
- Long CW, Li P, Chen MH, Dong LR, Hu DY, Song BA (2015) Synthesis, antitobacco 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 102:639–647. https://doi.org/10.1016/j.ejmech.2015.08.029 CrossRefGoogle Scholar
- Niu ZX, Li HB, Hu FZ, Yang HZ (2008) Synthesis and bioassay research of some benzotriazin-4-ones. Symposium on Organic Chemistry of the 26th Annual Conference of Chinese Chemical SocietyGoogle Scholar
- Sirisoma N, Pervin A, Zhang H, Jiang SC, Willardsen JA, Anderson MB, Mather G, Pleiman CM, Kasibhatla S, Tseng B, Drewe J, Cai SX (2010) Discovery of N-methyl-4-(4-methoxyanilino)quinazolines as potent apoptosis inducers. Structure–activity relationship of the quinazoline ring. Bioorg Med Chem Lett 20:2330–2334. https://doi.org/10.1016/j.bmcl.2010.01.155 CrossRefGoogle Scholar
- Wu ZX, Zhang J, Chen JX, Pan JK, Zhao L, Liu DY, Zhang AW, Chen J, Hu DY, Song BA (2017) Design, synthesis, antiviral bioactivity and three-dimensional quantitative structure–activity relationship study of novel ferulic acid ester derivatives containing quinazoline moiety. Pest Manag Sci 73:2079–2089. https://doi.org/10.1002/ps.4579 CrossRefGoogle Scholar
- Zhang J, Zhao L, Zhu C, Wu ZX, Zhang GP, Gan XH, Liu DY, Pan JK, Hu DY, Song BA (2017) Facile synthesis of novel vanillin derivatives incorporating a bis(2-hydroxyethyl) dithhioacetal moiety as antiviral agents. J Agric Food Chem 65:4582–4588. https://doi.org/10.1021/acs.jafc.7b01035 CrossRefGoogle Scholar
- Zuo JJ, Ren YG, Liu AP, Pei H, Bai JJ, Huang L, Han KY, Yu YP, Yin DL (2013) Synthesis and insecticidal activity of benzotriazinone-3-amine derivatives. Fine Chem Intermed 43(2):9–12. https://doi.org/10.19342/j.cnki.issn.1009-9212,2013.02.002 Google Scholar