Synthesis of novel fenfuram-diarylether hybrids as potent succinate dehydrogenase inhibitors |
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| Affiliation: | 1. Department of Applied Chemistry, China Agricultural University, Beijing 100193, People’s Republic of China;2. State Key Laboratory of the Discovery and Development of Novel Pesticide, Shenyang Sinochem Agrochemicals R&D Co. Ltd., Shenyang 110021, People’s Republic of China;1. College of Plant Protection, Northwest A&F University, Yangling, Shaanxi 712100, China;2. Shaanxi Research Center of Biopesticide Engineering & Technology, Northwest A&F University, Yangling, Shaanxi 712100, China;3. College of Forestry, Northwest A&F University, Yangling, Shaanxi 712100, China;4. State Key Laboratory of Crop Stress Biology for Arid Areas, Northwest A&F University, Yangling, Shaanxi 712100, China;1. Institute of BioPharmaceutical Research, Liaocheng University, 1 Hunan Road, Liaocheng, 252000, PR China;2. Key Laboratory of Structure-Based Drug Design & Discovery of Ministry of Education, School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, 103 Wenhua Road, Shenhe District, Shenyang, 110016, PR China;1. Key Laboratory of Pesticide & Chemical Biology, College of Chemistry, Ministry of Education, Central China Normal University, Wuhan 430079, PR China;2. Collaborative Innovation Center of Chemical Science and Engineering, Tianjing 30071, PR China |
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| Abstract: | Twelve novel fenfuram-diarylether hybrids were designed, synthesized and characterized by 1H NMR and MS. Their in vitro antifungal activities were evaluated against five phytopathogenic fungi by mycelial growth inhibition method. Most compounds showed significant antifungal effect on Rhizoctonia solani and Sclerotinia sclerotiorum. Compound 1c exhibited the most potent antifungal effect on R. solani with an EC50 value of 0.242 mg/L, superior to the commercial fungicide boscalid (EC50 = 1.758 mg/L) and the lead fungicide fenfuram (EC50 = 7.691 mg/L). Molecular docking revealed that compound 1c featured a higher affinity for succinate dehydrogenase (SDH) than fenfuram. Furthermore, it was shown that the 2-chlorophenyl group of compound 1c formed a π-π stacking with D/Tyr-128 and a Cl-π interaction with B/His-249, which made compound 1c more active than fenfuram against SDH. |
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| Keywords: | Fenfuram-diarylether hybrids Synthesis Antifungal activities Molecular docking |
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