Synthesis and Bioactivity of Novel Sulfonate Scaffold-Containing Pyrazolecarbamide Derivatives as Antifungal and Antiviral Agents
Novel pyrazolecarbamide derivatives bearing a sulfonate fragment were synthesized to identify potential antifungal and antiviral agents. All the structures of the key intermediates and target compounds were confirmed by nuclear magnetic resonance (NMR) and high-resolution mass spectrometry (HRMS). T...
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| Format: | Article |
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Frontiers Media S.A.
2022-06-01
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| Series: | Frontiers in Chemistry |
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| Online Access: | https://www.frontiersin.org/articles/10.3389/fchem.2022.928842/full |
| _version_ | 1811236634040991744 |
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| author | Zhi-Wei Lei Zhi-Wei Lei Jianmei Yao Huifang Liu Chiyu Ma Wen Yang |
| author_facet | Zhi-Wei Lei Zhi-Wei Lei Jianmei Yao Huifang Liu Chiyu Ma Wen Yang |
| author_sort | Zhi-Wei Lei |
| collection | DOAJ |
| description | Novel pyrazolecarbamide derivatives bearing a sulfonate fragment were synthesized to identify potential antifungal and antiviral agents. All the structures of the key intermediates and target compounds were confirmed by nuclear magnetic resonance (NMR) and high-resolution mass spectrometry (HRMS). The single-crystal X-ray diffraction of the compound T22 showed that pyrazole carbamide is a sulfonate. The in vitro antifungal activities of the target compounds against Colletotrichum camelliae, Pestalotiopsis theae, Gibberella zeae, and Rhizoctonia solani were evaluated at 50 μg/ml. Among the four pathogens, the target compounds exhibited the highest antifungal activity against Rhizoctonia solani. The compound T24 (EC50 = 0.45 mg/L) had higher antifungal activity than the commercial fungicide hymexazol (EC50 = 10.49 mg/L) against R. solani, almost similar to bixafen (EC50 = 0.25 mg/L). Additionally, the target compounds exhibited protective effects in vivo against TMV. Thus, this study reveals that pyrazolecarbamide derivatives bearing a sulfonate fragment exhibit potential antifungal and antiviral activities. |
| first_indexed | 2024-04-12T12:12:27Z |
| format | Article |
| id | doaj.art-69fdddcfb65f4cf78dc4e6caf733812b |
| institution | Directory Open Access Journal |
| issn | 2296-2646 |
| language | English |
| last_indexed | 2024-04-12T12:12:27Z |
| publishDate | 2022-06-01 |
| publisher | Frontiers Media S.A. |
| record_format | Article |
| series | Frontiers in Chemistry |
| spelling | doaj.art-69fdddcfb65f4cf78dc4e6caf733812b2022-12-22T03:33:33ZengFrontiers Media S.A.Frontiers in Chemistry2296-26462022-06-011010.3389/fchem.2022.928842928842Synthesis and Bioactivity of Novel Sulfonate Scaffold-Containing Pyrazolecarbamide Derivatives as Antifungal and Antiviral AgentsZhi-Wei Lei0Zhi-Wei Lei1Jianmei Yao2Huifang Liu3Chiyu Ma4Wen Yang5State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang, ChinaTea Research Institute, Guizhou Academy of Agricultural Sciences, Guiyang, ChinaTea Research Institute, Guizhou Academy of Agricultural Sciences, Guiyang, ChinaTea Research Institute, Guizhou Academy of Agricultural Sciences, Guiyang, ChinaTea Research Institute, Guizhou Academy of Agricultural Sciences, Guiyang, ChinaTea Research Institute, Guizhou Academy of Agricultural Sciences, Guiyang, ChinaNovel pyrazolecarbamide derivatives bearing a sulfonate fragment were synthesized to identify potential antifungal and antiviral agents. All the structures of the key intermediates and target compounds were confirmed by nuclear magnetic resonance (NMR) and high-resolution mass spectrometry (HRMS). The single-crystal X-ray diffraction of the compound T22 showed that pyrazole carbamide is a sulfonate. The in vitro antifungal activities of the target compounds against Colletotrichum camelliae, Pestalotiopsis theae, Gibberella zeae, and Rhizoctonia solani were evaluated at 50 μg/ml. Among the four pathogens, the target compounds exhibited the highest antifungal activity against Rhizoctonia solani. The compound T24 (EC50 = 0.45 mg/L) had higher antifungal activity than the commercial fungicide hymexazol (EC50 = 10.49 mg/L) against R. solani, almost similar to bixafen (EC50 = 0.25 mg/L). Additionally, the target compounds exhibited protective effects in vivo against TMV. Thus, this study reveals that pyrazolecarbamide derivatives bearing a sulfonate fragment exhibit potential antifungal and antiviral activities.https://www.frontiersin.org/articles/10.3389/fchem.2022.928842/fullpyrazolecarbamidesulfonateantifungal activityantiviral activitysynthesis |
| spellingShingle | Zhi-Wei Lei Zhi-Wei Lei Jianmei Yao Huifang Liu Chiyu Ma Wen Yang Synthesis and Bioactivity of Novel Sulfonate Scaffold-Containing Pyrazolecarbamide Derivatives as Antifungal and Antiviral Agents Frontiers in Chemistry pyrazolecarbamide sulfonate antifungal activity antiviral activity synthesis |
| title | Synthesis and Bioactivity of Novel Sulfonate Scaffold-Containing Pyrazolecarbamide Derivatives as Antifungal and Antiviral Agents |
| title_full | Synthesis and Bioactivity of Novel Sulfonate Scaffold-Containing Pyrazolecarbamide Derivatives as Antifungal and Antiviral Agents |
| title_fullStr | Synthesis and Bioactivity of Novel Sulfonate Scaffold-Containing Pyrazolecarbamide Derivatives as Antifungal and Antiviral Agents |
| title_full_unstemmed | Synthesis and Bioactivity of Novel Sulfonate Scaffold-Containing Pyrazolecarbamide Derivatives as Antifungal and Antiviral Agents |
| title_short | Synthesis and Bioactivity of Novel Sulfonate Scaffold-Containing Pyrazolecarbamide Derivatives as Antifungal and Antiviral Agents |
| title_sort | synthesis and bioactivity of novel sulfonate scaffold containing pyrazolecarbamide derivatives as antifungal and antiviral agents |
| topic | pyrazolecarbamide sulfonate antifungal activity antiviral activity synthesis |
| url | https://www.frontiersin.org/articles/10.3389/fchem.2022.928842/full |
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