Design, Synthesis, and Antifungal Activity of 4-Amino Coumarin Based Derivatives
A series of 30 succinate dehydrogenase inhibitors (SDHIs) of 4-amino coumarin-based derivatives were designed and synthesized. According to the analysis of fungicidal activity in vitro, most of the compounds expressed broad-spectrum antifungal activity against four plant pathogenic fungi (<i>A...
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MDPI AG
2022-04-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/9/2738 |
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| author | Lu Xu Jinmeng Yu Lu Jin Le Pan |
| author_facet | Lu Xu Jinmeng Yu Lu Jin Le Pan |
| author_sort | Lu Xu |
| collection | DOAJ |
| description | A series of 30 succinate dehydrogenase inhibitors (SDHIs) of 4-amino coumarin-based derivatives were designed and synthesized. According to the analysis of fungicidal activity in vitro, most of the compounds expressed broad-spectrum antifungal activity against four plant pathogenic fungi (<i>Alternaria alternata, Alternaria solani, Fusarium oxysporum,</i> and <i>Botrytis cinerea</i>) using the mycelium growth inhibition method. The results showed that compounds <b>3n</b> with the group of 2-ene-3-methyl-butyl and <b>4e</b> with the group of 2-bromo-1-oxo-hexyl displayed excellent activity against <i>Alternaria alternata</i> and <i>Alternaria solani</i>, with EC<sub>50</sub> values of 92~145 μg/mL. Molecular docking showed that the inhibitor <b>3n</b> was completely locked into the cavity of SDH, forming a conventional hydrogen bond interacting with the amino acid residue TYR58. The present work indicates that these derivatives would serve as novel potential fungicides targeting SDH. |
| first_indexed | 2024-03-10T03:54:27Z |
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| id | doaj.art-35fe4d3130374af4bf705b11105a6972 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T03:54:27Z |
| publishDate | 2022-04-01 |
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| series | Molecules |
| spelling | doaj.art-35fe4d3130374af4bf705b11105a69722023-11-23T08:49:00ZengMDPI AGMolecules1420-30492022-04-01279273810.3390/molecules27092738Design, Synthesis, and Antifungal Activity of 4-Amino Coumarin Based DerivativesLu Xu0Jinmeng Yu1Lu Jin2Le Pan3College of Chemistry and Chemical Engineering, Xinjiang Agricultural University, Urumqi 830052, ChinaCollege of Chemistry and Chemical Engineering, Xinjiang Agricultural University, Urumqi 830052, ChinaCollege of Chemistry and Chemical Engineering, Xinjiang Agricultural University, Urumqi 830052, ChinaCollege of Chemistry and Chemical Engineering, Xinjiang Agricultural University, Urumqi 830052, ChinaA series of 30 succinate dehydrogenase inhibitors (SDHIs) of 4-amino coumarin-based derivatives were designed and synthesized. According to the analysis of fungicidal activity in vitro, most of the compounds expressed broad-spectrum antifungal activity against four plant pathogenic fungi (<i>Alternaria alternata, Alternaria solani, Fusarium oxysporum,</i> and <i>Botrytis cinerea</i>) using the mycelium growth inhibition method. The results showed that compounds <b>3n</b> with the group of 2-ene-3-methyl-butyl and <b>4e</b> with the group of 2-bromo-1-oxo-hexyl displayed excellent activity against <i>Alternaria alternata</i> and <i>Alternaria solani</i>, with EC<sub>50</sub> values of 92~145 μg/mL. Molecular docking showed that the inhibitor <b>3n</b> was completely locked into the cavity of SDH, forming a conventional hydrogen bond interacting with the amino acid residue TYR58. The present work indicates that these derivatives would serve as novel potential fungicides targeting SDH.https://www.mdpi.com/1420-3049/27/9/2738succinate dehydrogenaseinhibitor4-amino coumarinfungicideantifungal activitymolecular docking |
| spellingShingle | Lu Xu Jinmeng Yu Lu Jin Le Pan Design, Synthesis, and Antifungal Activity of 4-Amino Coumarin Based Derivatives Molecules succinate dehydrogenase inhibitor 4-amino coumarin fungicide antifungal activity molecular docking |
| title | Design, Synthesis, and Antifungal Activity of 4-Amino Coumarin Based Derivatives |
| title_full | Design, Synthesis, and Antifungal Activity of 4-Amino Coumarin Based Derivatives |
| title_fullStr | Design, Synthesis, and Antifungal Activity of 4-Amino Coumarin Based Derivatives |
| title_full_unstemmed | Design, Synthesis, and Antifungal Activity of 4-Amino Coumarin Based Derivatives |
| title_short | Design, Synthesis, and Antifungal Activity of 4-Amino Coumarin Based Derivatives |
| title_sort | design synthesis and antifungal activity of 4 amino coumarin based derivatives |
| topic | succinate dehydrogenase inhibitor 4-amino coumarin fungicide antifungal activity molecular docking |
| url | https://www.mdpi.com/1420-3049/27/9/2738 |
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