Design, synthesis, and antifungal activities of chalcone derivatives containing piperidine and sulfonamide moiety
A series of chalcone derivatives containing piperidine sulfonamide were designed and synthesized from natural chalones, and their structures were characterized on NMR and HRMS. In vitro antifungal activity test results showed that most of the target compounds exhibited good antifungal activities aga...
| Main Authors: | , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Elsevier
2024-01-01
|
| Series: | Journal of Saudi Chemical Society |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S1319610323001953 |
| _version_ | 1797351543977017344 |
|---|---|
| author | Piao Mao Tianyu Deng Jiao Tian Yi Liu Hui Xin Youshan An Yuzhi Hu Yishan Qin Wei Xue |
| author_facet | Piao Mao Tianyu Deng Jiao Tian Yi Liu Hui Xin Youshan An Yuzhi Hu Yishan Qin Wei Xue |
| author_sort | Piao Mao |
| collection | DOAJ |
| description | A series of chalcone derivatives containing piperidine sulfonamide were designed and synthesized from natural chalones, and their structures were characterized on NMR and HRMS. In vitro antifungal activity test results showed that most of the target compounds exhibited good antifungal activities against a variety of fungi in vitro. X17 showed an excellent antifungal activity against S. sclerotiorum, Phomopsis sp, P. capsica with EC50 values of 10.43, 10.78, 12.02 µg/mL, respectively. It was better than those of azoxystrobin (19.34, 18.21, 63.44 µg/mL). In vivo antifungal activity test showed that X17 at the concentration of 200 µg/mL had better curative activities on rape leaves (90.8 %) than that of azoxystrobin (86.6 %). The protective activities on kiwifruits (88.3 %) were better than that of azoxystrobin (86.1 %). Mechanical studies showed that X17 inhibited the normal hypha growth by disrupting the cell membrane of S. sclerotiorum. |
| first_indexed | 2024-03-08T13:02:00Z |
| format | Article |
| id | doaj.art-26b3ec1938a443c6ba7d90f61448f5b7 |
| institution | Directory Open Access Journal |
| issn | 1319-6103 |
| language | English |
| last_indexed | 2024-03-08T13:02:00Z |
| publishDate | 2024-01-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Journal of Saudi Chemical Society |
| spelling | doaj.art-26b3ec1938a443c6ba7d90f61448f5b72024-01-19T04:51:48ZengElsevierJournal of Saudi Chemical Society1319-61032024-01-01281101791Design, synthesis, and antifungal activities of chalcone derivatives containing piperidine and sulfonamide moietyPiao Mao0Tianyu Deng1Jiao Tian2Yi Liu3Hui Xin4Youshan An5Yuzhi Hu6Yishan Qin7Wei Xue8National Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Guiyang 550025, ChinaNational Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Guiyang 550025, ChinaNational Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Guiyang 550025, ChinaNational Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Guiyang 550025, ChinaNational Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Guiyang 550025, ChinaNational Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Guiyang 550025, ChinaNational Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Guiyang 550025, ChinaNational Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Guiyang 550025, ChinaNational Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Guiyang 550025, China; Corresponding author.A series of chalcone derivatives containing piperidine sulfonamide were designed and synthesized from natural chalones, and their structures were characterized on NMR and HRMS. In vitro antifungal activity test results showed that most of the target compounds exhibited good antifungal activities against a variety of fungi in vitro. X17 showed an excellent antifungal activity against S. sclerotiorum, Phomopsis sp, P. capsica with EC50 values of 10.43, 10.78, 12.02 µg/mL, respectively. It was better than those of azoxystrobin (19.34, 18.21, 63.44 µg/mL). In vivo antifungal activity test showed that X17 at the concentration of 200 µg/mL had better curative activities on rape leaves (90.8 %) than that of azoxystrobin (86.6 %). The protective activities on kiwifruits (88.3 %) were better than that of azoxystrobin (86.1 %). Mechanical studies showed that X17 inhibited the normal hypha growth by disrupting the cell membrane of S. sclerotiorum.http://www.sciencedirect.com/science/article/pii/S1319610323001953ChalconePiperidineSulfonamideAntifungal activity |
| spellingShingle | Piao Mao Tianyu Deng Jiao Tian Yi Liu Hui Xin Youshan An Yuzhi Hu Yishan Qin Wei Xue Design, synthesis, and antifungal activities of chalcone derivatives containing piperidine and sulfonamide moiety Journal of Saudi Chemical Society Chalcone Piperidine Sulfonamide Antifungal activity |
| title | Design, synthesis, and antifungal activities of chalcone derivatives containing piperidine and sulfonamide moiety |
| title_full | Design, synthesis, and antifungal activities of chalcone derivatives containing piperidine and sulfonamide moiety |
| title_fullStr | Design, synthesis, and antifungal activities of chalcone derivatives containing piperidine and sulfonamide moiety |
| title_full_unstemmed | Design, synthesis, and antifungal activities of chalcone derivatives containing piperidine and sulfonamide moiety |
| title_short | Design, synthesis, and antifungal activities of chalcone derivatives containing piperidine and sulfonamide moiety |
| title_sort | design synthesis and antifungal activities of chalcone derivatives containing piperidine and sulfonamide moiety |
| topic | Chalcone Piperidine Sulfonamide Antifungal activity |
| url | http://www.sciencedirect.com/science/article/pii/S1319610323001953 |
| work_keys_str_mv | AT piaomao designsynthesisandantifungalactivitiesofchalconederivativescontainingpiperidineandsulfonamidemoiety AT tianyudeng designsynthesisandantifungalactivitiesofchalconederivativescontainingpiperidineandsulfonamidemoiety AT jiaotian designsynthesisandantifungalactivitiesofchalconederivativescontainingpiperidineandsulfonamidemoiety AT yiliu designsynthesisandantifungalactivitiesofchalconederivativescontainingpiperidineandsulfonamidemoiety AT huixin designsynthesisandantifungalactivitiesofchalconederivativescontainingpiperidineandsulfonamidemoiety AT youshanan designsynthesisandantifungalactivitiesofchalconederivativescontainingpiperidineandsulfonamidemoiety AT yuzhihu designsynthesisandantifungalactivitiesofchalconederivativescontainingpiperidineandsulfonamidemoiety AT yishanqin designsynthesisandantifungalactivitiesofchalconederivativescontainingpiperidineandsulfonamidemoiety AT weixue designsynthesisandantifungalactivitiesofchalconederivativescontainingpiperidineandsulfonamidemoiety |