Design,synthesis and fungicidal evaluation of novel pyraclostrobin analogues |
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Authors: | Lili Wang Shuangshuang Zhao Xiaotian Kong Lingling Cao Sheng Tian Yonghao Ye Chunhua Qiao |
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Institution: | 1. Jiangsu Key Laboratory of Preventive and Translational Medicine for Geriatric Diseases, College of Pharmaceutical Sciences, Soochow University, Suzhou 215123, PR China;2. College of Plant Protection, State & Local Joint Engineering Research Center of Green Pesticide Invention and Application, Nanjing Agricultural University, Nanjing 210095, PR China;3. Institute of Functional Nano and Soft Materials (FUNSOM), Soochow University, Suzhou, Jiangsu 215123, PR China |
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Abstract: | A series of novel pyraclostrobin derivatives were designed and prepared as antifungal agents. Their antifungal activities were tested in vitro with five important phytopathogenic fungi, namely, Batrylis cinerea, Phytophthora capsici, Fusarium sulphureum, Gloeosporium pestis and Sclerotinia sclerotiorum using the mycelium growth inhibition method. Among these compounds, 5s displayed IC50 value of 0.57?μg/mL against Batrylis cinerea and 5k-II displayed IC50 value of 0.43?μg/mL against Sclerotinia sclerotiorum, which were close to that of the positive control pyraclostrobin (0.18?μg/mL and 0.15?μg/mL). Other compounds 5f, 5k-II, 5j, 5m and 5s also exhibited strong antifungal activity. Further enzymatic assay demonstrated compound 5s inhibited porcine bc1 complex with IC50 value of 0.95?μM. The statistical results from an integrated computational pipeline demonstrated the predicted total binding free energy for compound 5s is the highest. Consequently, compound 5s with the biphenyl-4-methoxyl side chain could serve as a new motif as inhibitors of bc1 complex and deserve to be further investigated. |
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Keywords: | Antifungal activity Pyraclostrobin analogues Phytopathogenic fungi Molecular docking |
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