Design, Catalyst-Free Synthesis of New Novel α-Trifluoromethylated Tertiary Alcohols Bearing Coumarins as Potential Antifungal Agents
A new method for the synthesis of α-trifluoromethylated tertiary alcohols bearing coumarins is described. The reaction of 3-(trifluoroacetyl)coumarin and pyrrole provided the target compounds with high yields under catalyst-free, mild conditions. The crystal structure of compound <b>3fa</b&...
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-12-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/1/260 |
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| author | Shengfei Jiang Guoyu Yang Lijun Shi Liangxin Fan Zhenliang Pan Caixia Wang Xiaodan Chang Bingyi Zhou Meng Xu Lulu Wu Cuilian Xu |
| author_facet | Shengfei Jiang Guoyu Yang Lijun Shi Liangxin Fan Zhenliang Pan Caixia Wang Xiaodan Chang Bingyi Zhou Meng Xu Lulu Wu Cuilian Xu |
| author_sort | Shengfei Jiang |
| collection | DOAJ |
| description | A new method for the synthesis of α-trifluoromethylated tertiary alcohols bearing coumarins is described. The reaction of 3-(trifluoroacetyl)coumarin and pyrrole provided the target compounds with high yields under catalyst-free, mild conditions. The crystal structure of compound <b>3fa</b> was investigated by X-ray diffraction analysis. The biological activities, such as in vitro antifungal activity of the α-trifluoromethylated tertiary alcohols against Fusarium graminearum, Fusarium oxysporum, Fusarium moniliforme, Rhizoctonia solani Kuhn, and Phytophthora parasitica var nicotianae, were investigated. The bioassay results indicated that compounds <b>3ad</b>, <b>3gd</b>, and <b>3hd</b> showed broad-spectrum antifungal activity in vitro. Compound <b>3cd</b> exhibited excellent fungicidal activity against Rhizoctonia solani Kuhn, with an EC<sub>50</sub> value of 10.9 μg/mL, which was comparable to that of commercial fungicidal triadimefon (EC<sub>50</sub> = 6.1 μg/mL). Furthermore, molecular docking study suggested that <b>3cd</b> had high binding affinities with 1W9U, like argifin. |
| first_indexed | 2024-03-09T03:29:24Z |
| format | Article |
| id | doaj.art-63fe6651a2714e0dbf0633e59b153bdf |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T03:29:24Z |
| publishDate | 2022-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-63fe6651a2714e0dbf0633e59b153bdf2023-12-03T14:57:23ZengMDPI AGMolecules1420-30492022-12-0128126010.3390/molecules28010260Design, Catalyst-Free Synthesis of New Novel α-Trifluoromethylated Tertiary Alcohols Bearing Coumarins as Potential Antifungal AgentsShengfei Jiang0Guoyu Yang1Lijun Shi2Liangxin Fan3Zhenliang Pan4Caixia Wang5Xiaodan Chang6Bingyi Zhou7Meng Xu8Lulu Wu9Cuilian Xu10College of Sciences, Henan Agricultural University, Zhengzhou 450002, ChinaCollege of Sciences, Henan Agricultural University, Zhengzhou 450002, ChinaCollege of Sciences, Henan Agricultural University, Zhengzhou 450002, ChinaCollege of Sciences, Henan Agricultural University, Zhengzhou 450002, ChinaCollege of Sciences, Henan Agricultural University, Zhengzhou 450002, ChinaCollege of Sciences, Henan Agricultural University, Zhengzhou 450002, ChinaCollege of Sciences, Henan Agricultural University, Zhengzhou 450002, ChinaCollege of Sciences, Henan Agricultural University, Zhengzhou 450002, ChinaDepartment of Information, The First Affiliated Hospital, Zhengzhou University, Zhengzhou 450052, ChinaCollege of Sciences, Henan Agricultural University, Zhengzhou 450002, ChinaCollege of Sciences, Henan Agricultural University, Zhengzhou 450002, ChinaA new method for the synthesis of α-trifluoromethylated tertiary alcohols bearing coumarins is described. The reaction of 3-(trifluoroacetyl)coumarin and pyrrole provided the target compounds with high yields under catalyst-free, mild conditions. The crystal structure of compound <b>3fa</b> was investigated by X-ray diffraction analysis. The biological activities, such as in vitro antifungal activity of the α-trifluoromethylated tertiary alcohols against Fusarium graminearum, Fusarium oxysporum, Fusarium moniliforme, Rhizoctonia solani Kuhn, and Phytophthora parasitica var nicotianae, were investigated. The bioassay results indicated that compounds <b>3ad</b>, <b>3gd</b>, and <b>3hd</b> showed broad-spectrum antifungal activity in vitro. Compound <b>3cd</b> exhibited excellent fungicidal activity against Rhizoctonia solani Kuhn, with an EC<sub>50</sub> value of 10.9 μg/mL, which was comparable to that of commercial fungicidal triadimefon (EC<sub>50</sub> = 6.1 μg/mL). Furthermore, molecular docking study suggested that <b>3cd</b> had high binding affinities with 1W9U, like argifin.https://www.mdpi.com/1420-3049/28/1/260α-trifluoromethylated tertiary alcoholcoumarincatalyst-freeantifungal activity |
| spellingShingle | Shengfei Jiang Guoyu Yang Lijun Shi Liangxin Fan Zhenliang Pan Caixia Wang Xiaodan Chang Bingyi Zhou Meng Xu Lulu Wu Cuilian Xu Design, Catalyst-Free Synthesis of New Novel α-Trifluoromethylated Tertiary Alcohols Bearing Coumarins as Potential Antifungal Agents Molecules α-trifluoromethylated tertiary alcohol coumarin catalyst-free antifungal activity |
| title | Design, Catalyst-Free Synthesis of New Novel α-Trifluoromethylated Tertiary Alcohols Bearing Coumarins as Potential Antifungal Agents |
| title_full | Design, Catalyst-Free Synthesis of New Novel α-Trifluoromethylated Tertiary Alcohols Bearing Coumarins as Potential Antifungal Agents |
| title_fullStr | Design, Catalyst-Free Synthesis of New Novel α-Trifluoromethylated Tertiary Alcohols Bearing Coumarins as Potential Antifungal Agents |
| title_full_unstemmed | Design, Catalyst-Free Synthesis of New Novel α-Trifluoromethylated Tertiary Alcohols Bearing Coumarins as Potential Antifungal Agents |
| title_short | Design, Catalyst-Free Synthesis of New Novel α-Trifluoromethylated Tertiary Alcohols Bearing Coumarins as Potential Antifungal Agents |
| title_sort | design catalyst free synthesis of new novel α trifluoromethylated tertiary alcohols bearing coumarins as potential antifungal agents |
| topic | α-trifluoromethylated tertiary alcohol coumarin catalyst-free antifungal activity |
| url | https://www.mdpi.com/1420-3049/28/1/260 |
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