Design, Synthesis and Antifungal Activities of Novel Pyrazole Analogues Containing the Aryl Trifluoromethoxy Group
On the basis of the three-component synthetic methodology developed by us, a total of twenty-six pyrazole compounds bearing aryl OCF<sub>3</sub> were designed and synthesized. Their chemical structures were characterized by <sup>1</sup>H and <sup>13</sup>C nuclear...
| Main Authors: | , , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2023-08-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/28/17/6279 |
| _version_ | 1797582101598437376 |
|---|---|
| author | Tongchao Zhao Yuyao Sun Yufei Meng Lifang Liu Jingwen Dai Guoan Yan Xiaohong Pan Xiong Guan Liyan Song Ran Lin |
| author_facet | Tongchao Zhao Yuyao Sun Yufei Meng Lifang Liu Jingwen Dai Guoan Yan Xiaohong Pan Xiong Guan Liyan Song Ran Lin |
| author_sort | Tongchao Zhao |
| collection | DOAJ |
| description | On the basis of the three-component synthetic methodology developed by us, a total of twenty-six pyrazole compounds bearing aryl OCF<sub>3</sub> were designed and synthesized. Their chemical structures were characterized by <sup>1</sup>H and <sup>13</sup>C nuclear magnetic resonance and high-resolution mass spectrometry. These compounds were evaluated systematically for antifungal activities in vitro against six plant pathogenic fungi by the mycelium growth rate method. Most of the compounds showed some activity against each of the fungi at 100 μg/mL. Compounds <b>1t</b> and <b>1v</b> exhibited higher activity against all the tested fungi, and <b>1v</b> displayed the highest activity against <i>F. graminearum</i> with an EC<sub>50</sub> value of 0.0530 μM, which was comparable with commercial pyraclostrobin. Structure–activity relationship analysis showed that, with respect to the R<sub>1</sub> substituent, the straight chain or cycloalkyl ring moiety was a key structural moiety for the activity, and the R<sub>2</sub> substituent on the pyrazole ring could have significant effects on the activity. Simple and readily available pyrazoles with potent antifungal activity were obtained, which are ready for further elaboration to serve as a pharmacophore in new potential antifungal agents. |
| first_indexed | 2024-03-10T23:17:06Z |
| format | Article |
| id | doaj.art-214c7616cc5248a19899443188d35ed3 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T23:17:06Z |
| publishDate | 2023-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-214c7616cc5248a19899443188d35ed32023-11-19T08:33:46ZengMDPI AGMolecules1420-30492023-08-012817627910.3390/molecules28176279Design, Synthesis and Antifungal Activities of Novel Pyrazole Analogues Containing the Aryl Trifluoromethoxy GroupTongchao Zhao0Yuyao Sun1Yufei Meng2Lifang Liu3Jingwen Dai4Guoan Yan5Xiaohong Pan6Xiong Guan7Liyan Song8Ran Lin9Key Laboratory of Biopesticide and Chemical Biology, Ministry of Education, College of Plant Protection, Fujian Agriculture and Forestry University, Fuzhou 350002, ChinaKey Laboratory of Biopesticide and Chemical Biology, Ministry of Education, College of Plant Protection, Fujian Agriculture and Forestry University, Fuzhou 350002, ChinaKey Laboratory of Biopesticide and Chemical Biology, Ministry of Education, College of Plant Protection, Fujian Agriculture and Forestry University, Fuzhou 350002, ChinaKey Laboratory of Biopesticide and Chemical Biology, Ministry of Education, College of Plant Protection, Fujian Agriculture and Forestry University, Fuzhou 350002, ChinaKey Laboratory of Biopesticide and Chemical Biology, Ministry of Education, College of Plant Protection, Fujian Agriculture and Forestry University, Fuzhou 350002, ChinaKey Laboratory of Biopesticide and Chemical Biology, Ministry of Education, College of Plant Protection, Fujian Agriculture and Forestry University, Fuzhou 350002, ChinaKey Laboratory of Biopesticide and Chemical Biology, Ministry of Education, College of Plant Protection, Fujian Agriculture and Forestry University, Fuzhou 350002, ChinaKey Laboratory of Biopesticide and Chemical Biology, Ministry of Education, College of Plant Protection, Fujian Agriculture and Forestry University, Fuzhou 350002, ChinaKey Laboratory of Biopesticide and Chemical Biology, Ministry of Education, College of Plant Protection, Fujian Agriculture and Forestry University, Fuzhou 350002, ChinaKey Laboratory of Biopesticide and Chemical Biology, Ministry of Education, College of Plant Protection, Fujian Agriculture and Forestry University, Fuzhou 350002, ChinaOn the basis of the three-component synthetic methodology developed by us, a total of twenty-six pyrazole compounds bearing aryl OCF<sub>3</sub> were designed and synthesized. Their chemical structures were characterized by <sup>1</sup>H and <sup>13</sup>C nuclear magnetic resonance and high-resolution mass spectrometry. These compounds were evaluated systematically for antifungal activities in vitro against six plant pathogenic fungi by the mycelium growth rate method. Most of the compounds showed some activity against each of the fungi at 100 μg/mL. Compounds <b>1t</b> and <b>1v</b> exhibited higher activity against all the tested fungi, and <b>1v</b> displayed the highest activity against <i>F. graminearum</i> with an EC<sub>50</sub> value of 0.0530 μM, which was comparable with commercial pyraclostrobin. Structure–activity relationship analysis showed that, with respect to the R<sub>1</sub> substituent, the straight chain or cycloalkyl ring moiety was a key structural moiety for the activity, and the R<sub>2</sub> substituent on the pyrazole ring could have significant effects on the activity. Simple and readily available pyrazoles with potent antifungal activity were obtained, which are ready for further elaboration to serve as a pharmacophore in new potential antifungal agents.https://www.mdpi.com/1420-3049/28/17/6279pyrazole analoguespathogenic fungiantifungal activitystructure–activity relationship |
| spellingShingle | Tongchao Zhao Yuyao Sun Yufei Meng Lifang Liu Jingwen Dai Guoan Yan Xiaohong Pan Xiong Guan Liyan Song Ran Lin Design, Synthesis and Antifungal Activities of Novel Pyrazole Analogues Containing the Aryl Trifluoromethoxy Group Molecules pyrazole analogues pathogenic fungi antifungal activity structure–activity relationship |
| title | Design, Synthesis and Antifungal Activities of Novel Pyrazole Analogues Containing the Aryl Trifluoromethoxy Group |
| title_full | Design, Synthesis and Antifungal Activities of Novel Pyrazole Analogues Containing the Aryl Trifluoromethoxy Group |
| title_fullStr | Design, Synthesis and Antifungal Activities of Novel Pyrazole Analogues Containing the Aryl Trifluoromethoxy Group |
| title_full_unstemmed | Design, Synthesis and Antifungal Activities of Novel Pyrazole Analogues Containing the Aryl Trifluoromethoxy Group |
| title_short | Design, Synthesis and Antifungal Activities of Novel Pyrazole Analogues Containing the Aryl Trifluoromethoxy Group |
| title_sort | design synthesis and antifungal activities of novel pyrazole analogues containing the aryl trifluoromethoxy group |
| topic | pyrazole analogues pathogenic fungi antifungal activity structure–activity relationship |
| url | https://www.mdpi.com/1420-3049/28/17/6279 |
| work_keys_str_mv | AT tongchaozhao designsynthesisandantifungalactivitiesofnovelpyrazoleanaloguescontainingthearyltrifluoromethoxygroup AT yuyaosun designsynthesisandantifungalactivitiesofnovelpyrazoleanaloguescontainingthearyltrifluoromethoxygroup AT yufeimeng designsynthesisandantifungalactivitiesofnovelpyrazoleanaloguescontainingthearyltrifluoromethoxygroup AT lifangliu designsynthesisandantifungalactivitiesofnovelpyrazoleanaloguescontainingthearyltrifluoromethoxygroup AT jingwendai designsynthesisandantifungalactivitiesofnovelpyrazoleanaloguescontainingthearyltrifluoromethoxygroup AT guoanyan designsynthesisandantifungalactivitiesofnovelpyrazoleanaloguescontainingthearyltrifluoromethoxygroup AT xiaohongpan designsynthesisandantifungalactivitiesofnovelpyrazoleanaloguescontainingthearyltrifluoromethoxygroup AT xiongguan designsynthesisandantifungalactivitiesofnovelpyrazoleanaloguescontainingthearyltrifluoromethoxygroup AT liyansong designsynthesisandantifungalactivitiesofnovelpyrazoleanaloguescontainingthearyltrifluoromethoxygroup AT ranlin designsynthesisandantifungalactivitiesofnovelpyrazoleanaloguescontainingthearyltrifluoromethoxygroup |