Design, synthesis, and antibacterial activity of novel 8-methoxyquinoline-2-carboxamide compounds containing 1,3,4-thiadiazole moiety
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Tengfei Qu
Abstract
A series of novel 8-methoxyquinoline-2-carboxamide compounds containing 1,3,4-thiadiazole moiety was designed and synthesized by using an active substructure combination method. Then, the antibacterial activities of all the target compounds were evaluated in vitro against three Gram-positive bacteria and three Gram-negative bacteria. The antibacterial assay showed that some target compounds displayed moderate to good antibacterial efficacy in comparison with the reference drug Chloromycin. Some interesting results of structure-activity relationships were also discussed.
Acknowledgments
This project was partly supported by the Project of Key Laboratory at the University of Education Department of Xinjiang Uygur Autonomous Region (No. 2016YSHXZD03).
References
1. Meziane-Cherif D, Courvalin P. Antibiotic resistance: to the rescue of old drugs. Nature 2014;510:477–8.10.1038/510477aSearch in Google Scholar PubMed
2. Cho I, Yamanishi S, Cox L, Methé BA, Zavadil J, Li K, et al. Antibiotics in early life alter the murine colonic microbiome and adiposity. Nature 2012;488:621–6.10.1038/nature11400Search in Google Scholar PubMed PubMed Central
3. Kant R, Singh V, Nath G, Awasthi SK, Agarwal A. Design, synthesis and biological evaluation of ciprofloxacin tethered bis-1,2,3-triazole conjugates as potent antibacterial agents. Eur J Med Chem 2016;124:218–28.10.1016/j.ejmech.2016.08.031Search in Google Scholar PubMed
4. Kumar D, Jain SK. A comprehensive review of N-heterocycles as cytotoxic agents. Curr Med Chem 2016;23:4338–94.10.2174/0929867323666160809093930Search in Google Scholar PubMed
5. Oliveri V, Vecchio G. 8-Hydroxyquinolines in medicinal chemistry: a structural perspective. Eur J Med Chem 2016;120:252–74.10.1016/j.ejmech.2016.05.007Search in Google Scholar PubMed
6. Song Y, Xu H, Chen W, Zhan P, Liu X. 8-Hydroxyquinoline: a privileged structure with a broad-ranging pharmacological potential. Med Chem Commun 2015;6:61–74.10.1039/C4MD00284ASearch in Google Scholar
7. Chan FT, Guan MX, Mackenzie AM, Diaz-Mitoma F. Susceptibility testing of Dientamoeba fragilis ATCC 30948 with iodoquinol, paromomycin, tetracycline, and metronidazole. Antimicrob Agents Ch 1994;38:1157–60.10.1128/AAC.38.5.1157Search in Google Scholar PubMed PubMed Central
8. Hu Y, Li CY, Wang XM, Yang YH, Zhu HL. 1,3,4-thiadiazole: synthesis, reactions, and applications in medicinal, agricultural, and materials chemistry. Chem Rev 2014;114:5572–610.10.1021/cr400131uSearch in Google Scholar PubMed
9. Shawali AS. 1, 3, 4-Thiadiazoles of pharmacological interest: recent trends in their synthesis via tandem 1,3-dipolar cycloaddition: Review. Journal of advanced research 2014;5:1–17.10.1016/j.jare.2013.01.004Search in Google Scholar PubMed PubMed Central
10. Haider S, Alam MS, Hamid H. 1,3,4-Thiadiazoles: a potent multi targeted pharmacological scaffold. Eur J Med Chem 2015;92:156–77.10.1016/j.ejmech.2014.12.035Search in Google Scholar PubMed
11. Cockerill FR, Hindler JA, Patel JB, Alder J, Powell M, Dudley MN, et al. Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically; approved standard – ninth edition: M07–A9. Wayne, PA: Clinical and Laboratory Standards Institute (CLSI) Press, 2012:16–20.Search in Google Scholar
12. Guo Y, Wang X, Qu L, Xu S, Zhao Y, Xie R, et al. Design, synthesis, antibacterial and insecticidal activities of novel N-phenylpyrazole fraxinellone hybrid compounds. RSC Advances 2017;7:11796–802.10.1039/C6RA28064ASearch in Google Scholar
©2018 Walter de Gruyter GmbH, Berlin/Boston
Articles in the same Issue
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- Fast RBC loading by fluorescent antibodies and nuclei staining dye and their potential bioanalytical applications
- Chemical profiling of Di-Wu-Yang-Gan Granules by ultra performance liquid chromatography coupled to quadrupole time-of-flight mass spectrometry with MSE technology
- Design, synthesis, and antibacterial activity of novel 8-methoxyquinoline-2-carboxamide compounds containing 1,3,4-thiadiazole moiety
- Pseudomonas and Burkholderia inhibit growth and asexual development of Phytophthora capsici
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Articles in the same Issue
- Frontmatter
- Fast RBC loading by fluorescent antibodies and nuclei staining dye and their potential bioanalytical applications
- Chemical profiling of Di-Wu-Yang-Gan Granules by ultra performance liquid chromatography coupled to quadrupole time-of-flight mass spectrometry with MSE technology
- Design, synthesis, and antibacterial activity of novel 8-methoxyquinoline-2-carboxamide compounds containing 1,3,4-thiadiazole moiety
- Pseudomonas and Burkholderia inhibit growth and asexual development of Phytophthora capsici
- Antiproliferative activity of synthesized some new benzimidazole carboxamidines against MCF-7 breast carcinoma cells
- Overexpression of c-Myc enhances recombinant protein production in High Five cells after baculovirus infection
- Kostchyienones A and B, new antiplasmodial and cytotoxicity of limonoids from the roots of Pseudocedrela kotschyi (Schweinf.) Harms
- Antimicrobial and antioxidant activities of two polyketides from lichen-endophytic fungus Preussia sp.
