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Synthesis and biological activity of myricetin derivatives containing 1,3,4-thiadiazole scaffold
BACKGROUND: Myricetin and 1,3,4-thiadiazole derivatives were reported to exhibit favorable antiviral and antibacterial activities. Aiming to discover novel myricetin analogues with potent activities, a series of novel myricetin derivatives containing 1,3,4-thiadiazole moiety were synthesized, and th...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Springer International Publishing
2017
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5645266/ https://www.ncbi.nlm.nih.gov/pubmed/29086886 http://dx.doi.org/10.1186/s13065-017-0336-7 |
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author | Zhong, Xinmin Wang, Xiaobin Chen, Lijuan Ruan, Xianghui Li, Qin Zhang, Juping Chen, Zhuo Xue, Wei |
author_facet | Zhong, Xinmin Wang, Xiaobin Chen, Lijuan Ruan, Xianghui Li, Qin Zhang, Juping Chen, Zhuo Xue, Wei |
author_sort | Zhong, Xinmin |
collection | PubMed |
description | BACKGROUND: Myricetin and 1,3,4-thiadiazole derivatives were reported to exhibit favorable antiviral and antibacterial activities. Aiming to discover novel myricetin analogues with potent activities, a series of novel myricetin derivatives containing 1,3,4-thiadiazole moiety were synthesized, and their antibacterial and antiviral activities were evaluated. RESULT: Bioassay results indicated that some target compounds exhibited potential antibacterial and antiviral activities. Among them, compounds 2, 3a, 3b, 3d, 3f, 3i, 3m and 3p exhibited excellent antibacterial activities against Xanthomonas oryzae pv. Oryzae (Xoo), with EC(50) values of 42.7, 38.6, 20.8, 12.9, 22.7, 27.3, 18.3 and 29.4 μg/mL, respectively, which were better than that of thiadiazole-copper (94.9 μg/mL). Compounds 3b, 3d, 3e, 3f, 3i and 3o showed good antibacterial activities against Ralstonia solanacearum (Rs), with EC(50) values of 37.9, 72.6, 43.6, 59.6, 60.6 and 39.6 μg/mL, respectively, which were superior to that of thiadiazole-copper (131.7 μg/mL). In addition, compounds 3d, 3f, 3i and 3m showed better curative activities against tobacco mosaic virus (TMV), with EC(50) values of 152.8, 99.7, 127.1, and 167.3 μg/mL, respectively, which were better than that of ningnanmycin (211.1 μg/mL). CONCLUSIONS: A series of myricetin derivatives containing 1,3,4-thiadiazole scaffold were synthesized, and their antibacterial activities against Xoo and Rs and their antiviral activity against TMV were evaluated. Bioassays indicated that some target compounds exhibited potential antibacterial and antiviral activities. These results indicated this kind of myricetin analogues could be further studied as potential alternative templates in the search for novel antibacterial and antiviral agents. ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (doi:10.1186/s13065-017-0336-7) contains supplementary material, which is available to authorized users. |
format | Online Article Text |
id | pubmed-5645266 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | Springer International Publishing |
record_format | MEDLINE/PubMed |
spelling | pubmed-56452662017-10-30 Synthesis and biological activity of myricetin derivatives containing 1,3,4-thiadiazole scaffold Zhong, Xinmin Wang, Xiaobin Chen, Lijuan Ruan, Xianghui Li, Qin Zhang, Juping Chen, Zhuo Xue, Wei Chem Cent J Research Article BACKGROUND: Myricetin and 1,3,4-thiadiazole derivatives were reported to exhibit favorable antiviral and antibacterial activities. Aiming to discover novel myricetin analogues with potent activities, a series of novel myricetin derivatives containing 1,3,4-thiadiazole moiety were synthesized, and their antibacterial and antiviral activities were evaluated. RESULT: Bioassay results indicated that some target compounds exhibited potential antibacterial and antiviral activities. Among them, compounds 2, 3a, 3b, 3d, 3f, 3i, 3m and 3p exhibited excellent antibacterial activities against Xanthomonas oryzae pv. Oryzae (Xoo), with EC(50) values of 42.7, 38.6, 20.8, 12.9, 22.7, 27.3, 18.3 and 29.4 μg/mL, respectively, which were better than that of thiadiazole-copper (94.9 μg/mL). Compounds 3b, 3d, 3e, 3f, 3i and 3o showed good antibacterial activities against Ralstonia solanacearum (Rs), with EC(50) values of 37.9, 72.6, 43.6, 59.6, 60.6 and 39.6 μg/mL, respectively, which were superior to that of thiadiazole-copper (131.7 μg/mL). In addition, compounds 3d, 3f, 3i and 3m showed better curative activities against tobacco mosaic virus (TMV), with EC(50) values of 152.8, 99.7, 127.1, and 167.3 μg/mL, respectively, which were better than that of ningnanmycin (211.1 μg/mL). CONCLUSIONS: A series of myricetin derivatives containing 1,3,4-thiadiazole scaffold were synthesized, and their antibacterial activities against Xoo and Rs and their antiviral activity against TMV were evaluated. Bioassays indicated that some target compounds exhibited potential antibacterial and antiviral activities. These results indicated this kind of myricetin analogues could be further studied as potential alternative templates in the search for novel antibacterial and antiviral agents. ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (doi:10.1186/s13065-017-0336-7) contains supplementary material, which is available to authorized users. Springer International Publishing 2017-10-17 /pmc/articles/PMC5645266/ /pubmed/29086886 http://dx.doi.org/10.1186/s13065-017-0336-7 Text en © The Author(s) 2017 Open AccessThis article is distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The Creative Commons Public Domain Dedication waiver (http://creativecommons.org/publicdomain/zero/1.0/) applies to the data made available in this article, unless otherwise stated. |
spellingShingle | Research Article Zhong, Xinmin Wang, Xiaobin Chen, Lijuan Ruan, Xianghui Li, Qin Zhang, Juping Chen, Zhuo Xue, Wei Synthesis and biological activity of myricetin derivatives containing 1,3,4-thiadiazole scaffold |
title | Synthesis and biological activity of myricetin derivatives containing 1,3,4-thiadiazole scaffold |
title_full | Synthesis and biological activity of myricetin derivatives containing 1,3,4-thiadiazole scaffold |
title_fullStr | Synthesis and biological activity of myricetin derivatives containing 1,3,4-thiadiazole scaffold |
title_full_unstemmed | Synthesis and biological activity of myricetin derivatives containing 1,3,4-thiadiazole scaffold |
title_short | Synthesis and biological activity of myricetin derivatives containing 1,3,4-thiadiazole scaffold |
title_sort | synthesis and biological activity of myricetin derivatives containing 1,3,4-thiadiazole scaffold |
topic | Research Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5645266/ https://www.ncbi.nlm.nih.gov/pubmed/29086886 http://dx.doi.org/10.1186/s13065-017-0336-7 |
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