Cargando…

Design, Synthesis, and Bioactivity Evaluation of New Thiochromanone Derivatives Containing a Carboxamide Moiety

In this study, using the botanical active component thiochromanone as the lead compound, a total of 32 new thiochromanone derivatives containing a carboxamide moiety were designed and synthesized and their in vitro antibacterial activities against Xanthomonas oryzae pv. oryzae (Xoo), Xanthomonas ory...

Descripción completa

Detalles Bibliográficos
Autores principales: Xiao, Lingling, Yu, Lu, Li, Pei, Chi, Jiyan, Tang, Zhangfei, Li, Jie, Tan, Shuming, Wang, Xiaodan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8348251/
https://www.ncbi.nlm.nih.gov/pubmed/34361545
http://dx.doi.org/10.3390/molecules26154391
_version_ 1783735295394447360
author Xiao, Lingling
Yu, Lu
Li, Pei
Chi, Jiyan
Tang, Zhangfei
Li, Jie
Tan, Shuming
Wang, Xiaodan
author_facet Xiao, Lingling
Yu, Lu
Li, Pei
Chi, Jiyan
Tang, Zhangfei
Li, Jie
Tan, Shuming
Wang, Xiaodan
author_sort Xiao, Lingling
collection PubMed
description In this study, using the botanical active component thiochromanone as the lead compound, a total of 32 new thiochromanone derivatives containing a carboxamide moiety were designed and synthesized and their in vitro antibacterial activities against Xanthomonas oryzae pv. oryzae (Xoo), Xanthomonas oryzae pv. oryzicolaby (Xoc), and Xanthomonas axonopodis pv. citri (Xac) were determined, as well as their in vitro antifungal activities against Botryosphaeria dothidea (B. dothidea), Phomopsis sp., and Botrytis cinerea (B. cinerea). Bioassay results demonstrated that some of the target compounds exhibited moderate to good in vitro antibacterial and antifungal activities. In particular, compound 4e revealed excellent in vitro antibacterial activity against Xoo, Xoc, and Xac, and its EC(50) values of 15, 19, and 23 μg/mL, respectively, were superior to those of Bismerthiazol and Thiodiazole copper. Meanwhile, compound 3b revealed moderate in vitro antifungal activity against B. dothidea at 50 μg/mL, and the inhibition rate reached 88%, which was even better than that of Pyrimethanil, however, lower than that of Carbendazim. To the best of our knowledge, this is the first report on the antibacterial and antifungal activities of this series of novel thiochromanone derivatives containing a carboxamide moiety.
format Online
Article
Text
id pubmed-8348251
institution National Center for Biotechnology Information
language English
publishDate 2021
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-83482512021-08-08 Design, Synthesis, and Bioactivity Evaluation of New Thiochromanone Derivatives Containing a Carboxamide Moiety Xiao, Lingling Yu, Lu Li, Pei Chi, Jiyan Tang, Zhangfei Li, Jie Tan, Shuming Wang, Xiaodan Molecules Article In this study, using the botanical active component thiochromanone as the lead compound, a total of 32 new thiochromanone derivatives containing a carboxamide moiety were designed and synthesized and their in vitro antibacterial activities against Xanthomonas oryzae pv. oryzae (Xoo), Xanthomonas oryzae pv. oryzicolaby (Xoc), and Xanthomonas axonopodis pv. citri (Xac) were determined, as well as their in vitro antifungal activities against Botryosphaeria dothidea (B. dothidea), Phomopsis sp., and Botrytis cinerea (B. cinerea). Bioassay results demonstrated that some of the target compounds exhibited moderate to good in vitro antibacterial and antifungal activities. In particular, compound 4e revealed excellent in vitro antibacterial activity against Xoo, Xoc, and Xac, and its EC(50) values of 15, 19, and 23 μg/mL, respectively, were superior to those of Bismerthiazol and Thiodiazole copper. Meanwhile, compound 3b revealed moderate in vitro antifungal activity against B. dothidea at 50 μg/mL, and the inhibition rate reached 88%, which was even better than that of Pyrimethanil, however, lower than that of Carbendazim. To the best of our knowledge, this is the first report on the antibacterial and antifungal activities of this series of novel thiochromanone derivatives containing a carboxamide moiety. MDPI 2021-07-21 /pmc/articles/PMC8348251/ /pubmed/34361545 http://dx.doi.org/10.3390/molecules26154391 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Xiao, Lingling
Yu, Lu
Li, Pei
Chi, Jiyan
Tang, Zhangfei
Li, Jie
Tan, Shuming
Wang, Xiaodan
Design, Synthesis, and Bioactivity Evaluation of New Thiochromanone Derivatives Containing a Carboxamide Moiety
title Design, Synthesis, and Bioactivity Evaluation of New Thiochromanone Derivatives Containing a Carboxamide Moiety
title_full Design, Synthesis, and Bioactivity Evaluation of New Thiochromanone Derivatives Containing a Carboxamide Moiety
title_fullStr Design, Synthesis, and Bioactivity Evaluation of New Thiochromanone Derivatives Containing a Carboxamide Moiety
title_full_unstemmed Design, Synthesis, and Bioactivity Evaluation of New Thiochromanone Derivatives Containing a Carboxamide Moiety
title_short Design, Synthesis, and Bioactivity Evaluation of New Thiochromanone Derivatives Containing a Carboxamide Moiety
title_sort design, synthesis, and bioactivity evaluation of new thiochromanone derivatives containing a carboxamide moiety
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8348251/
https://www.ncbi.nlm.nih.gov/pubmed/34361545
http://dx.doi.org/10.3390/molecules26154391
work_keys_str_mv AT xiaolingling designsynthesisandbioactivityevaluationofnewthiochromanonederivativescontainingacarboxamidemoiety
AT yulu designsynthesisandbioactivityevaluationofnewthiochromanonederivativescontainingacarboxamidemoiety
AT lipei designsynthesisandbioactivityevaluationofnewthiochromanonederivativescontainingacarboxamidemoiety
AT chijiyan designsynthesisandbioactivityevaluationofnewthiochromanonederivativescontainingacarboxamidemoiety
AT tangzhangfei designsynthesisandbioactivityevaluationofnewthiochromanonederivativescontainingacarboxamidemoiety
AT lijie designsynthesisandbioactivityevaluationofnewthiochromanonederivativescontainingacarboxamidemoiety
AT tanshuming designsynthesisandbioactivityevaluationofnewthiochromanonederivativescontainingacarboxamidemoiety
AT wangxiaodan designsynthesisandbioactivityevaluationofnewthiochromanonederivativescontainingacarboxamidemoiety