Synthesis of novel fenfuram-diarylether hybrids as potent succinate dehydrogenase inhibitors

被引：37

作者：

Jin, Hong ^{[1
]}

Zhou, Jingya ^{[1
]}

Pu, Tao ^{[1
]}

Zhang, Aigui ^{[1
]}

Gao, Xuheng ^{[1
]}

Tao, Ke ^{[1
]}

Hou, Taiping ^{[1
]}

机构：

[1] Sichuan Univ, Coll Life Sci, Key Lab Bioresource & Ecoenvironm, Minist Educ, Chengdu 610064, Sichuan, Peoples R China

来源：

BIOORGANIC CHEMISTRY | 2017年 / 73卷

关键词：

Fenfuram-diarylether hybrids; Synthesis; Antifungal activities; Molecular docking; ANTIFUNGAL ACTIVITY; DERIVATIVES; FUNGICIDES; CARBOXIN; DESIGN;

D O I：

10.1016/j.bioorg.2017.06.002

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Twelve novel fenfuram-diarylether hybrids were designed, synthesized and characterized by H-1 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 p-p stacking with D/Tyr- 128 and a Cl-pi interaction with B/His-249, which made compound 1c more active than fenfuram against SDH. (C) 2017 Elsevier Inc. All rights reserved.

引用

页码：76 / 82

页数：7

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