Design, synthesis and antifungal activities of novel cis-enamides via intermediate derivatization method
On the basis of the structure of natural product lansiumamide B (1), a total of 27 novel cis-enamide compounds were designed and synthesized via Intermediate Derivatization Method. Their chemical structures were characterized by 1H and 13C nuclear magnetic resonance and high-resolution mass spectrom...
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| Format: | Article |
| Language: | English |
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KeAi Communications Co., Ltd.
2023-03-01
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| Series: | Advanced Agrochem |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2773237123000059 |
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| author | Huiyou Xu Yuyao Sun Hongzuo Li Yunrong Lai Tongchao Zhao Yufei Meng Xiaohong Pan Ran Lin Liyan Song |
| author_facet | Huiyou Xu Yuyao Sun Hongzuo Li Yunrong Lai Tongchao Zhao Yufei Meng Xiaohong Pan Ran Lin Liyan Song |
| author_sort | Huiyou Xu |
| collection | DOAJ |
| description | On the basis of the structure of natural product lansiumamide B (1), a total of 27 novel cis-enamide compounds were designed and synthesized via Intermediate Derivatization Method. Their chemical structures were characterized by 1H and 13C nuclear magnetic resonance and high-resolution mass spectrometry. The in vitro antifungal activities against Sclerotinia sclerotiorum, Thanatephorus cucumeris and Botrytis cinerea were evaluated by the mycelium linear growth rate method. Most of the compounds showed some activity against each of the fungi at 25 or 50 μg/mL. The relationship between structure and antifungal activity was also discussed, which showed the cinnamic double bond was critical to maintain the antifungal activity. Notably, among the title compounds, 3e and 3h could inhibit mycelia growth of Botrytis cinerea by approximately 50% (EC50) at 39.17 and 41.25 μg/mL respectively, which showed better antifungal activity than lansiumamide B (1) with more concise chemical structure. The present study pointed out the correct direction for the development and optimization of lansiumamide B derivatives as potential inhibitors of pathogenic fungi. |
| first_indexed | 2024-04-24T16:48:01Z |
| format | Article |
| id | doaj.art-0af1f12fa0d24de5b4848b7db5cba97a |
| institution | Directory Open Access Journal |
| issn | 2773-2371 |
| language | English |
| last_indexed | 2024-04-24T16:48:01Z |
| publishDate | 2023-03-01 |
| publisher | KeAi Communications Co., Ltd. |
| record_format | Article |
| series | Advanced Agrochem |
| spelling | doaj.art-0af1f12fa0d24de5b4848b7db5cba97a2024-03-29T05:51:37ZengKeAi Communications Co., Ltd.Advanced Agrochem2773-23712023-03-012197103Design, synthesis and antifungal activities of novel cis-enamides via intermediate derivatization methodHuiyou Xu0Yuyao Sun1Hongzuo Li2Yunrong Lai3Tongchao Zhao4Yufei Meng5Xiaohong Pan6Ran Lin7Liyan Song8Key Laboratory of Biopesticide and Chemical Biology, Ministry of Education, College of Plant Protection, Fujian Agriculture and Forestry University, Fuzhou, Fujian, ChinaKey Laboratory of Biopesticide and Chemical Biology, Ministry of Education, College of Plant Protection, Fujian Agriculture and Forestry University, Fuzhou, Fujian, ChinaKey Laboratory of Biopesticide and Chemical Biology, Ministry of Education, College of Plant Protection, Fujian Agriculture and Forestry University, Fuzhou, Fujian, ChinaKey Laboratory of Biopesticide and Chemical Biology, Ministry of Education, College of Plant Protection, Fujian Agriculture and Forestry University, Fuzhou, Fujian, ChinaKey Laboratory of Biopesticide and Chemical Biology, Ministry of Education, College of Plant Protection, Fujian Agriculture and Forestry University, Fuzhou, Fujian, ChinaKey Laboratory of Biopesticide and Chemical Biology, Ministry of Education, College of Plant Protection, Fujian Agriculture and Forestry University, Fuzhou, Fujian, ChinaKey Laboratory of Biopesticide and Chemical Biology, Ministry of Education, College of Plant Protection, Fujian Agriculture and Forestry University, Fuzhou, Fujian, ChinaCorresponding author.; Key Laboratory of Biopesticide and Chemical Biology, Ministry of Education, College of Plant Protection, Fujian Agriculture and Forestry University, Fuzhou, Fujian, ChinaCorresponding author.; Key Laboratory of Biopesticide and Chemical Biology, Ministry of Education, College of Plant Protection, Fujian Agriculture and Forestry University, Fuzhou, Fujian, ChinaOn the basis of the structure of natural product lansiumamide B (1), a total of 27 novel cis-enamide compounds were designed and synthesized via Intermediate Derivatization Method. Their chemical structures were characterized by 1H and 13C nuclear magnetic resonance and high-resolution mass spectrometry. The in vitro antifungal activities against Sclerotinia sclerotiorum, Thanatephorus cucumeris and Botrytis cinerea were evaluated by the mycelium linear growth rate method. Most of the compounds showed some activity against each of the fungi at 25 or 50 μg/mL. The relationship between structure and antifungal activity was also discussed, which showed the cinnamic double bond was critical to maintain the antifungal activity. Notably, among the title compounds, 3e and 3h could inhibit mycelia growth of Botrytis cinerea by approximately 50% (EC50) at 39.17 and 41.25 μg/mL respectively, which showed better antifungal activity than lansiumamide B (1) with more concise chemical structure. The present study pointed out the correct direction for the development and optimization of lansiumamide B derivatives as potential inhibitors of pathogenic fungi.http://www.sciencedirect.com/science/article/pii/S2773237123000059Lansiumamide Bcis-enamideSynthesisAntifungalStructure activity relationship |
| spellingShingle | Huiyou Xu Yuyao Sun Hongzuo Li Yunrong Lai Tongchao Zhao Yufei Meng Xiaohong Pan Ran Lin Liyan Song Design, synthesis and antifungal activities of novel cis-enamides via intermediate derivatization method Advanced Agrochem Lansiumamide B cis-enamide Synthesis Antifungal Structure activity relationship |
| title | Design, synthesis and antifungal activities of novel cis-enamides via intermediate derivatization method |
| title_full | Design, synthesis and antifungal activities of novel cis-enamides via intermediate derivatization method |
| title_fullStr | Design, synthesis and antifungal activities of novel cis-enamides via intermediate derivatization method |
| title_full_unstemmed | Design, synthesis and antifungal activities of novel cis-enamides via intermediate derivatization method |
| title_short | Design, synthesis and antifungal activities of novel cis-enamides via intermediate derivatization method |
| title_sort | design synthesis and antifungal activities of novel cis enamides via intermediate derivatization method |
| topic | Lansiumamide B cis-enamide Synthesis Antifungal Structure activity relationship |
| url | http://www.sciencedirect.com/science/article/pii/S2773237123000059 |
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