Synthesis and antibacterial activity of novel chalcone derivatives bearing a coumarin moiety
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A series of novel chalcone derivatives, that bear a coumarin moiety, were designed and synthesized, and their structures were confirmed via 1H NMR, 13C NMR, and H RMS. The bioassay results indicated that most title compounds exhibited remarkable antibacterial effects. Notably, compound 3a presented the most efficient antibacterial activity against Xanthomonas oryzae pv. Oryzae (Xoo), with median effect concentration (EC50) value of 49.77 μg/mL, which was far preferable than that of thiodiazole–copper (179.93 μg/mL). Meanwhile, compound 3n was identified as the best potential antibacterial agent against Xanthomonas axonopodis pv. citri (Xac), with EC50 value of 48.04 μg/mL, which far surpassed that of thiodiazole–copper (162.48 μg/mL). Furthermore, compound 3i indicated excellent antibacterial activity against Ralstonia solanacearum (Rs), with EC50 value of 65.04 μg/mL, which was far superior to that of thiodiazole–copper (126.89 μg/mL). This study indicated that chalcone hybrids, bearing a coumarin moiety, are worthy of further investigation as potential antibacterial drugs.
KeywordsSynthesis Chalcone Coumarin Antibacterial activity
The authors gratefully acknowledge the financial support of the National Key Research and Development Program of China (no. 2017YFD0200506), the National Nature Science Foundation of China (nos. 21867003, 21462012).
- Bandgar BP, Patil SA, Gacche RN, Korbad BL, Hote BS, Kinkar SN, Jalde SS (2010) Synthesis and biological evaluation of nitrogen-containing chalcones as possible anti-inflammatory and antioxidant agents. Bioorg Med Chem Lett 20:730–733. https://doi.org/10.1016/j.bmcl.2009.11.068 CrossRefGoogle Scholar
- Karki R, Song C, Kadayat TM, Magar TBT, Bist G, Shrestha A, Na Y, Kwon Y, Lee E (2015) Topoisomerase I and II inhibitory activity, cytotoxicity, and structure-activity relationship study of dihydroxylated 2, 6-diphenyl-4-aryl pyridines. Bioorg Med Chem 23:3638–3654. https://doi.org/10.1016/j.bmc.2015.04.002 CrossRefGoogle Scholar
- Konieczny MT, Konieczny W, Sabisz M, Skladanowski A, Wakieć R, Augustynowicz-Kopeć E, Zwolska Z (2007) Acid-catalyzed synthesis of oxathiolone fused chalcones. Comparison of their activity toward various microorganisms and human cancer cells line. Eur J Med Chem 42:729–733. https://doi.org/10.1016/j.ejmech.2006.12.014 CrossRefGoogle Scholar
- Li P, Shi L, Yang X, Yang L, Chen XW, Wu F, Shi QC, Xu WM, He M, Hu DY, Song BA (2014) Design, synthesis, and antibacterial activity against rice bacterial leaf blight and leaf streak of 2,5-substituted-1,3,4-oxadiazole/thiadiazole sulfone derivatives. Bioorg Med Chem Lett 24:1677–1680. https://doi.org/10.1016/j.bmcl.2014.02.060 CrossRefGoogle Scholar
- Pingaew R, Saekee A, Mandi P, Nantasenamat C, Prachayasittikul S, Ruchirawat S, Prachayasittikul V (2014) Synthesis, biological evaluation and molecular docking of novel chalcone coumarin hybrids as anticancer and antimalarial agents. Eur J Med Chem 85:65–76. https://doi.org/10.1016/j.ejmech.2014.07.087 CrossRefGoogle Scholar
- Tavares LDC, Johann S, Alves TMDA, Guerra JC, Souza-Fagundes EMD, Cisalpino PS, Bortoluzzi AJ, Caramori GF, Piccoli RDM, Braibante HTS, Braibante MEF, Pizzolatti MG (2011) Quinolinyl and quinolinyl N-oxide chalcones: synthesis, antifungal and cytotoxic activities. Eur J Med Chem 46:4448–4456. https://doi.org/10.1016/j.ejmech.2011.07.019 CrossRefGoogle Scholar
- Vazquez-Rodriguez S, López RL, Matos MJ, Armesto-Quintas G, Serra S, Uriarte E, Santana L, Borges F, Crego AM, Santos Y (2015) Design, synthesis and antibacterial study of new potent and selective coumarin-chalcone derivatives for the treatment of tenacibaculosis. Bioorg Med Chem 23:7045–7052. https://doi.org/10.1016/j.bmc.2015.09.028 CrossRefGoogle Scholar
- Zhang JP, Li Q, Zhang C, Li P, Chen LJ, Wang YH, Ruan XH, Xiao W, Xue W (2018) Synthesis, antibacterial, and antiviral activities of novel penta-1,4-dien-3-one derivatives containing a benzotriazin-4(3H)-one moiety. Chem Pap 72:2193–2202. https://doi.org/10.1007/s11696-018-0422-x CrossRefGoogle Scholar