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Design, synthesis and evaluation of carbazole derivatives as potential antimicrobial agents
Five series of novel carbazole derivatives containing an aminoguanidine, dihydrotriazine, thiosemicarbazide, semicarbazide or isonicotinic moiety were designed, synthesised and evaluated for their antimicrobial activities. Most of the compounds exhibited potent inhibitory activities towards differen...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Taylor & Francis
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7801072/ https://www.ncbi.nlm.nih.gov/pubmed/33404277 http://dx.doi.org/10.1080/14756366.2020.1850713 |
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author | Xue, Yi-Jie Li, Ming-Yue Jin, Xue-Jun Zheng, Chang-Ji Piao, Hu-Ri |
author_facet | Xue, Yi-Jie Li, Ming-Yue Jin, Xue-Jun Zheng, Chang-Ji Piao, Hu-Ri |
author_sort | Xue, Yi-Jie |
collection | PubMed |
description | Five series of novel carbazole derivatives containing an aminoguanidine, dihydrotriazine, thiosemicarbazide, semicarbazide or isonicotinic moiety were designed, synthesised and evaluated for their antimicrobial activities. Most of the compounds exhibited potent inhibitory activities towards different bacterial strains (including one multidrug-resistant clinical isolate) and one fungal strain with minimum inhibitory concentrations (MICs) between 0.5 and 16 µg/ml. Compounds 8f and 9d showed the most potent inhibitory activities (MICs of 0.5–2 µg/ml). Furthermore, compounds 8b, 8d, 8f, 8k, 9b and 9e with antimicrobial activities were not cytotoxic to human gastric cancer cell lines (SGC-7901 and AGS) or a normal human liver cell line (L-02). Structure–activity relationship analyses and docking studies implicated the dihydrotriazine group in increasing the antimicrobial potency and reducing the toxicity of the carbazole compounds. In vitro enzyme activity assays suggested that compound 8f binding to dihydrofolate reductase might account for the antimicrobial effect. |
format | Online Article Text |
id | pubmed-7801072 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | Taylor & Francis |
record_format | MEDLINE/PubMed |
spelling | pubmed-78010722021-01-21 Design, synthesis and evaluation of carbazole derivatives as potential antimicrobial agents Xue, Yi-Jie Li, Ming-Yue Jin, Xue-Jun Zheng, Chang-Ji Piao, Hu-Ri J Enzyme Inhib Med Chem Research Paper Five series of novel carbazole derivatives containing an aminoguanidine, dihydrotriazine, thiosemicarbazide, semicarbazide or isonicotinic moiety were designed, synthesised and evaluated for their antimicrobial activities. Most of the compounds exhibited potent inhibitory activities towards different bacterial strains (including one multidrug-resistant clinical isolate) and one fungal strain with minimum inhibitory concentrations (MICs) between 0.5 and 16 µg/ml. Compounds 8f and 9d showed the most potent inhibitory activities (MICs of 0.5–2 µg/ml). Furthermore, compounds 8b, 8d, 8f, 8k, 9b and 9e with antimicrobial activities were not cytotoxic to human gastric cancer cell lines (SGC-7901 and AGS) or a normal human liver cell line (L-02). Structure–activity relationship analyses and docking studies implicated the dihydrotriazine group in increasing the antimicrobial potency and reducing the toxicity of the carbazole compounds. In vitro enzyme activity assays suggested that compound 8f binding to dihydrofolate reductase might account for the antimicrobial effect. Taylor & Francis 2021-01-06 /pmc/articles/PMC7801072/ /pubmed/33404277 http://dx.doi.org/10.1080/14756366.2020.1850713 Text en © 2020 The Author(s). Published by Informa UK Limited, trading as Taylor & Francis Group. https://creativecommons.org/licenses/by/4.0/This is an Open Access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) ), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Research Paper Xue, Yi-Jie Li, Ming-Yue Jin, Xue-Jun Zheng, Chang-Ji Piao, Hu-Ri Design, synthesis and evaluation of carbazole derivatives as potential antimicrobial agents |
title | Design, synthesis and evaluation of carbazole derivatives as potential antimicrobial agents |
title_full | Design, synthesis and evaluation of carbazole derivatives as potential antimicrobial agents |
title_fullStr | Design, synthesis and evaluation of carbazole derivatives as potential antimicrobial agents |
title_full_unstemmed | Design, synthesis and evaluation of carbazole derivatives as potential antimicrobial agents |
title_short | Design, synthesis and evaluation of carbazole derivatives as potential antimicrobial agents |
title_sort | design, synthesis and evaluation of carbazole derivatives as potential antimicrobial agents |
topic | Research Paper |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7801072/ https://www.ncbi.nlm.nih.gov/pubmed/33404277 http://dx.doi.org/10.1080/14756366.2020.1850713 |
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