Статья

Design, Synthesis, Antifungal Activity, and Molecular Docking of Streptochlorin Derivatives Containing the Nitrile Group

Jing‐Rui LiuJiangsu Key Laboratory of Pesticide Science, College of Sciences, Nanjing Agricultural University, Nanjing 210095, ChinaYa GaoJiangsu Key Laboratory of Pesticide Science, College of Sciences, Nanjing Agricultural University, Nanjing 210095, ChinaBing JinJiangsu Key Laboratory of Pesticide Science, College of Sciences, Nanjing Agricultural University, Nanjing 210095, ChinaDa‐Le GuoState Key Laboratory Breeding Base of Systematic Research Development and Utilization of Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, ChinaFang DengState Key Laboratory Breeding Base of Systematic Research Development and Utilization of Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, ChinaQiang BianNational Pesticide Engineering Research Center (Tianjin), College of Chemistry, Nankai University, Tianjin 300071, ChinaHaifeng ZhangDepartment of Plant Pathology, College of Plant Protection, Nanjing Agricultural University, Nanjing 210095, ChinaXinya HanSchool of Chemistry & Chemical Engineering, Anhui University of Technology, Ma’anshan 243002, ChinaAbdallah S. AliDepartment of Microbiology, Faculty of Agriculture, Cairo University, Giza 12613, EgyptMing‐Zhi ZhangJiangsu Key Laboratory of Pesticide Science, College of Sciences, Nanjing Agricultural University, Nanjing 210095, ChinaWeihua ZhangJiangsu Key Laboratory of Pesticide Science, College of Sciences, Nanjing Agricultural University, Nanjing 210095, ChinaYu‐Cheng GuSyngenta Jealott’s Hill International Research Centre, Bracknell RG42 6EY, Berkshire, UK

2023en

ABI

Аннотация

Based on the structures of natural products streptochlorin and pimprinine derived from marine or soil microorganisms, a series of streptochlorin derivatives containing the nitrile group were designed and synthesized through acylation and oxidative annulation. Evaluation for antifungal activity showed that compound 3a could be regarded as the most promising candidate—it demonstrated over 85% growth inhibition against Botrytis cinerea, Gibberella zeae, and Colletotrichum lagenarium, as well as a broad antifungal spectrum in primary screening at the concentration of 50 μg/mL. The SAR study revealed that non-substituent or alkyl substituent at the 2-position of oxazole ring were favorable for antifungal activity, while aryl and monosubstituted aryl were detrimental to activity. Molecular docking models indicated that 3a formed hydrogen bonds and hydrophobic interactions with Leucyl-tRNA Synthetase, offering a perspective for the possible mechanism of action for antifungal activity of the target compounds.

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Идентификаторы

DOI: 10.3390/md21020103

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