Synthesis of novel indole derivatives containing double 1,3,4-oxadiazole moiety as efficient bactericides against phytopathogenic bacterium Xanthomonas oryzae
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A series of novel indole derivatives containing double 1,3,4-oxadiazole moiety was designed, synthesized and evaluated for their antibacterial activities in vitro. These compounds were fully characterized by 1H NMR, 13C NMR, and HRMS. Bioassay results indicated that most of title compounds exhibited excellent antibacterial activities against rice bacterial pathogen Xanthomonas oryzae (Xoo). For example, compounds 7d, 7h, 7i, 7j, 7k, 7l and 7m had the half-maximal effective concentration (EC50) values of 52.31, 54.12, 40.65, 38.80, 51.13, 52.75 and 50.66 µg/mL, respectively, which was better than that of commercial product bismerthiazol (BMT) (85.18 µg/mL). The experimental results proved that indole derivatives bearing double 1,3,4-oxadiazole unit are promising candidates for the development of new agricultural bactericides against pathogenic bacterium Xoo.
KeywordsIndole 1,3,4-Oxadiazole Antibacterial activity
This research was financially supported by the Project Enterprises and Business (H 110029), the Scientific Research Foundation of Guizhou University (no. 201542), and Guizhou Science Technology Program (no. 20161055), the Young Talents Scientific Research Foundation of Guizhou Education Department (no. 2017).
- Hong W, Li J, Chang Z, Tan XL, Yang H, Ouyang YF, Yang YH, Kaur S, Paterson IC, Ngeow YF, Wang H (2017) Synthesis and biological evaluation of indole core-based derivatives with potent antibacterial activity against resistant bacterial pathogens. J Antibiot 70:832–844. https://doi.org/10.1038/ja.2017.55 Google Scholar
- Karg EM, Luderer S, Pergola C, Bühring U, Rossi A, Northoff H, Sautebin L, Troscütz (2009) Structural optimization and biological evaluation of 2-substituted 5-hydroxyindole-3-carboxylates as potent inhibitors of human 5-lipoxygenase. J Med Chem 52:3474–3483. https://doi.org/10.1021/jm900212y Google 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 derivative. Bioorg Med Chem Lett 24:1677–1680. https://doi.org/10.1016/j.bmcl.2014.02.060 Google Scholar
- Li P, Shi L, Gao MN, Yang X, Xue W, Jin LH, Hu DY, Song BA (2015) Antibacterial activities against rice bacterial leaf blight and tomato bacterial wilt of 2-mercapto-5-substituted-1,3,4-oxadiazole/thiadiazole derivatives. Bioorg Med Chem Lett 25:481–484. https://doi.org/10.1016/j.bmcl.2014.12.038 Google Scholar
- Mew TW (1987) Current status and future prospects of research on bacterial blight of rice. Annu Rev Phytopathol 25:359–382. https://doi.org/10.1146/annurev.py.25.090187.002043 Google Scholar
- Patel RV, Patel AB, Kumari P, Chikhalia KH (2012) Synthesis of novel 3-(5-sulfanyl-1,3,4-oxadiazol-2-yl)-2H-chromen-2-one condensed s-triazinyl piperazines and piperidines as antimicrobial agents. Med Chem Res 21:3119–3132Google Scholar
- Salzberg SL, Sommer DD, Schatz MC, Phillippy AM, Rabinowicz PD, Tsuge S, Furutani A, Ochiai H, Delcher AL, Kelley D, Madupu R, Puiu D, Radune D, Shumway M, Trapnell C, Aparna G, Jha G, Pandey A, Patil PB, Ishihara H, Meyer DF, Szurek B, Verdier V, Koebnik R, Dow JM, Ryan RP, Hirata H, Tsuyumu S, Lee SW, Ronald PC, Sonti RV, Sluys MV, Leach JE, White FF, Bogdanove AJ (2008) Genome sequence and rapid evolution of the rice pathogen Xanthomonas oryzae PXO99 A. BMC Genom 9:204. https://doi.org/10.1186/1471-2164-9-204 Google Scholar
- Wang XB, Zhong XM, Zhu XS, Wang H, Li Q, Zhang JP, Ruan XH, Xue W (2017) Synthesis and antibacterial activity of oxime ester derivatives containing 1,2,4-triazole or 1,3,4-oxadiazole moiety. Chem Pap 2017:1–8Google Scholar
- Williams JD, Nguyen ST, Gu S, Ding XY, Butler MM, Tashjian TF, Opperman TJ, Panchal RG, Bavari S, Peet NP, Moir DT, Bowlin TL (2013) Potent and broad-spectrum antibacterial activity of indole-based bisamidine antibiotics: synthesis and SAR of novel analogs of MBX 1066 and MBX 1090. Bioorg Med Chem 21:7790–7806. https://doi.org/10.1016/j.bmc.2013.10.014 Google Scholar
- Yang L, Bao XP (2017) Synthesis of novel 1,2,4-triazole derivatives containing the quinazolinylpiperidinyl moiety and N-(substituted phenyl)acetamide group as efficient bactericides against the phytopathogenic bacterium Xanthomonas oryzae. RSC Adv 7:34005–34011. https://doi.org/10.1039/c7ra04819j Google Scholar
- Zhu YJ, Guo XF, Fan ZJ, Chen L, Ma LY, Wang HX, Wei Y, Xu XM, Lin JP, Bakulev VA (2016) Approach to thiazole-containing tetrahydropyridines via Aza–Rauhut–Currier reaction and their potent fungicidal and insecticidal activity. RSC Adv 6:112704–112711. https://doi.org/10.1039/c6ra24342h Google Scholar