1,2,4-Oxadiazole-Based Bio-Isosteres of Benzamides: Synthesis, Biological Activity and Toxicity to Zebrafish Embryo

To discover new compounds with broad spectrum and high activity, we designed a series of novel benzamides containing 1,2,4-oxadiazole moiety by bioisosterism, and 28 benzamides derivatives with antifungal activity were synthesized. These compounds were evaluated against four fungi: Botrytis cinereal...

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Autores principales: Yang, Sen, Ren, Chao-Li, Ma, Tian-Yang, Zou, Wen-Qian, Dai, Li, Tian, Xiao-Yu, Liu, Xing-Hai, Tan, Cheng-Xia
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
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Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7956408/
https://www.ncbi.nlm.nih.gov/pubmed/33673430
http://dx.doi.org/10.3390/ijms22052367
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author Yang, Sen
Ren, Chao-Li
Ma, Tian-Yang
Zou, Wen-Qian
Dai, Li
Tian, Xiao-Yu
Liu, Xing-Hai
Tan, Cheng-Xia
author_facet Yang, Sen
Ren, Chao-Li
Ma, Tian-Yang
Zou, Wen-Qian
Dai, Li
Tian, Xiao-Yu
Liu, Xing-Hai
Tan, Cheng-Xia
author_sort Yang, Sen
collection PubMed
description To discover new compounds with broad spectrum and high activity, we designed a series of novel benzamides containing 1,2,4-oxadiazole moiety by bioisosterism, and 28 benzamides derivatives with antifungal activity were synthesized. These compounds were evaluated against four fungi: Botrytis cinereal, FusaHum graminearum, Marssonina mali, and Thanatephorus cucumeris. The results indicated that most of the compounds displayed good fungicidal activities, especially against Botrytis cinereal. For example, 10a (84.4%), 10d (83.6%), 10e (83.3%), 10f (83.1%), 10i (83.3%), and 10l (83.6%) were better than pyraclostrobin (81.4%) at 100 mg/L. In addition, the acute toxicity of 10f to zebrafish embryo was 20.58 mg/L, which was classified as a low-toxicity compound.
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spelling pubmed-79564082021-03-16 1,2,4-Oxadiazole-Based Bio-Isosteres of Benzamides: Synthesis, Biological Activity and Toxicity to Zebrafish Embryo Yang, Sen Ren, Chao-Li Ma, Tian-Yang Zou, Wen-Qian Dai, Li Tian, Xiao-Yu Liu, Xing-Hai Tan, Cheng-Xia Int J Mol Sci Article To discover new compounds with broad spectrum and high activity, we designed a series of novel benzamides containing 1,2,4-oxadiazole moiety by bioisosterism, and 28 benzamides derivatives with antifungal activity were synthesized. These compounds were evaluated against four fungi: Botrytis cinereal, FusaHum graminearum, Marssonina mali, and Thanatephorus cucumeris. The results indicated that most of the compounds displayed good fungicidal activities, especially against Botrytis cinereal. For example, 10a (84.4%), 10d (83.6%), 10e (83.3%), 10f (83.1%), 10i (83.3%), and 10l (83.6%) were better than pyraclostrobin (81.4%) at 100 mg/L. In addition, the acute toxicity of 10f to zebrafish embryo was 20.58 mg/L, which was classified as a low-toxicity compound. MDPI 2021-02-27 /pmc/articles/PMC7956408/ /pubmed/33673430 http://dx.doi.org/10.3390/ijms22052367 Text en © 2021 by the authors. 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 (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Yang, Sen
Ren, Chao-Li
Ma, Tian-Yang
Zou, Wen-Qian
Dai, Li
Tian, Xiao-Yu
Liu, Xing-Hai
Tan, Cheng-Xia
1,2,4-Oxadiazole-Based Bio-Isosteres of Benzamides: Synthesis, Biological Activity and Toxicity to Zebrafish Embryo
title 1,2,4-Oxadiazole-Based Bio-Isosteres of Benzamides: Synthesis, Biological Activity and Toxicity to Zebrafish Embryo
title_full 1,2,4-Oxadiazole-Based Bio-Isosteres of Benzamides: Synthesis, Biological Activity and Toxicity to Zebrafish Embryo
title_fullStr 1,2,4-Oxadiazole-Based Bio-Isosteres of Benzamides: Synthesis, Biological Activity and Toxicity to Zebrafish Embryo
title_full_unstemmed 1,2,4-Oxadiazole-Based Bio-Isosteres of Benzamides: Synthesis, Biological Activity and Toxicity to Zebrafish Embryo
title_short 1,2,4-Oxadiazole-Based Bio-Isosteres of Benzamides: Synthesis, Biological Activity and Toxicity to Zebrafish Embryo
title_sort 1,2,4-oxadiazole-based bio-isosteres of benzamides: synthesis, biological activity and toxicity to zebrafish embryo
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7956408/
https://www.ncbi.nlm.nih.gov/pubmed/33673430
http://dx.doi.org/10.3390/ijms22052367
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