Synthesis, Structural Determination, and Antifungal Activity of Novel Fluorinated Quinoline Analogs

A series of new fluorinated quinoline analogs were synthesized using Tebufloquin as the lead compound, 2-fluoroaniline, ethyl 2-methylacetoacetate, and substituted benzoic acid as raw materials. Their structures were confirmed by (1)H NMR, (13)C NMR, and HRMS. The compound 8-fluoro-2,3-dimethylquino...

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Autores principales: Sun, Xinpeng, Yu, Wei, Min, Lijing, Han, Liang, Hua, Xuewen, Shi, Jianjun, Sun, Nabo, Liu, Xinghai
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
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Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10145707/
https://www.ncbi.nlm.nih.gov/pubmed/37110607
http://dx.doi.org/10.3390/molecules28083373
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author Sun, Xinpeng
Yu, Wei
Min, Lijing
Han, Liang
Hua, Xuewen
Shi, Jianjun
Sun, Nabo
Liu, Xinghai
author_facet Sun, Xinpeng
Yu, Wei
Min, Lijing
Han, Liang
Hua, Xuewen
Shi, Jianjun
Sun, Nabo
Liu, Xinghai
author_sort Sun, Xinpeng
collection PubMed
description A series of new fluorinated quinoline analogs were synthesized using Tebufloquin as the lead compound, 2-fluoroaniline, ethyl 2-methylacetoacetate, and substituted benzoic acid as raw materials. Their structures were confirmed by (1)H NMR, (13)C NMR, and HRMS. The compound 8-fluoro-2,3-dimethylquinolin-4-yl 4-(tert-butyl)benzoate (2b) was further determined by X-ray single-crystal diffraction. The antifungal activity was tested at 50 μg/mL, and the bioassay results showed that these quinoline derivatives had good antifungal activity. Among them, compounds 2b, 2e, 2f, 2k, and 2n exhibited good activity (>80%) against S. sclerotiorum, and compound 2g displayed good activity (80.8%) against R. solani.
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spelling pubmed-101457072023-04-29 Synthesis, Structural Determination, and Antifungal Activity of Novel Fluorinated Quinoline Analogs Sun, Xinpeng Yu, Wei Min, Lijing Han, Liang Hua, Xuewen Shi, Jianjun Sun, Nabo Liu, Xinghai Molecules Article A series of new fluorinated quinoline analogs were synthesized using Tebufloquin as the lead compound, 2-fluoroaniline, ethyl 2-methylacetoacetate, and substituted benzoic acid as raw materials. Their structures were confirmed by (1)H NMR, (13)C NMR, and HRMS. The compound 8-fluoro-2,3-dimethylquinolin-4-yl 4-(tert-butyl)benzoate (2b) was further determined by X-ray single-crystal diffraction. The antifungal activity was tested at 50 μg/mL, and the bioassay results showed that these quinoline derivatives had good antifungal activity. Among them, compounds 2b, 2e, 2f, 2k, and 2n exhibited good activity (>80%) against S. sclerotiorum, and compound 2g displayed good activity (80.8%) against R. solani. MDPI 2023-04-11 /pmc/articles/PMC10145707/ /pubmed/37110607 http://dx.doi.org/10.3390/molecules28083373 Text en © 2023 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
Sun, Xinpeng
Yu, Wei
Min, Lijing
Han, Liang
Hua, Xuewen
Shi, Jianjun
Sun, Nabo
Liu, Xinghai
Synthesis, Structural Determination, and Antifungal Activity of Novel Fluorinated Quinoline Analogs
title Synthesis, Structural Determination, and Antifungal Activity of Novel Fluorinated Quinoline Analogs
title_full Synthesis, Structural Determination, and Antifungal Activity of Novel Fluorinated Quinoline Analogs
title_fullStr Synthesis, Structural Determination, and Antifungal Activity of Novel Fluorinated Quinoline Analogs
title_full_unstemmed Synthesis, Structural Determination, and Antifungal Activity of Novel Fluorinated Quinoline Analogs
title_short Synthesis, Structural Determination, and Antifungal Activity of Novel Fluorinated Quinoline Analogs
title_sort synthesis, structural determination, and antifungal activity of novel fluorinated quinoline analogs
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10145707/
https://www.ncbi.nlm.nih.gov/pubmed/37110607
http://dx.doi.org/10.3390/molecules28083373
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