Synthesis and antimicrobial evaluation of novel 1,2,4-triazole thioether derivatives bearing a quinazoline moiety

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Abstract

A series of structurally novel 3-thioether-1-(quinazolin-4-yl)-1H-1,2,4-triazol-5-amine derivatives (7a–7r) were designed and synthesized based on a pharmacophore hybrid approach, and screened for their antibacterial and antifungal activities in vitro. All the target compounds were fully characterized through \(^{\mathrm {1}}\)H NMR, \(^{\mathrm {13}}\)C NMR and HRMS spectra. Among them, the structure of compound 7b was further confirmed via single-crystal X-ray diffraction analysis. The obtained results indicated that several target compounds demonstrated notable inhibition activities against tested phytopathogenic bacteria, using a turbidimetric method. For example, compounds 7d, 7g and 7i exhibited EC\(_{\mathrm {50 }}\) (half-maximal effective concentration) values of 46.9, 47.8 and 43.2 µg/mL, respectively, against the bacterium Xanthomonas axonopodis pv. citri (Xac), which were more potent than commercial agrobactericide Bismerthiazol (56.9 µg/mL). Moreover, EC\(_{\mathrm {50 }}\) values of compounds 7a and 7h were found to be 81.6 and 93.1 µg/mL, respectively, against the bacterium Ralstonia solanacearum (Rs), being over twofold more active than commercial agrobactericide Thiodiazole-copper (189.6 µg/mL). Finally, some compounds displayed a certain degree of inhibition activity against tested phytopathogenic fungi at 50 µg/mL.

Graphical abstract

Keywords

1, 2, 4-Triazole thioether Quinazoline Synthesis Antibacterial activity 

Notes

Acknowledgements

This work was financially supported by the National Natural Science Foundation of China (No. 21362003).

Supplementary material

11030_2018_9821_MOESM1_ESM.doc (6.1 mb)
Supplementary material 1 (doc 6246 KB)

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© Springer International Publishing AG, part of Springer Nature 2018

Authors and Affiliations

  1. 1.State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Centre for Research and Development of Fine ChemicalsGuizhou UniversityGuiyangChina

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