title: Synthesis, characterization, antifungal evaluation and 3D-QSAR study of phenylhydrazine substituted tetronic acid derivatives.
abstract: A series of 3-(1-(2-(substituted phenyl)hydrazinyl)alkylidene)furan-2,4(3H,5H)-diones were designed and prepared using two synthetic routes. Their structures were confirmed by FT-IR, (1)H NMR, (13)C NMR, MS, elemental analysis and single-crystal X-ray diffraction. Their bioactivity was evaluated against Botrytis cinerea in vitro. Most target compounds exhibited remarkable antifungal activity. Two compounds 7f and 7h were highly effective and their EC50 values were 0.241 μg/mL and 0.167 μg/mL, respectively, close to that of the control drug procymidone. 3D-QSAR studies of CoMFA and CoMSIA were carried out. Models with good predictive ability were generated with the cross validated q(2) values for CoMFA and CoMSIA being 0.565 and 0.823. Conventional r(2) values were 0.983 and 0.945, respectively. The results provided a practical tool for guiding the design and synthesis of novel and more potent tetronic acid derivatives containing substituted phenylhydrazine moiety.
authors.affiliation: Jiangsu Key Laboratory of Pesticide Science, Nanjing Agricultural, Nanjing 210095, PR China; Department of Science, College of Science, Nanjing Agricultural University, Nanjing 210095, PR China.
authors.forename: Ying
authors.initials: Y
authors.lastname: Hu
authors.affiliation: Ministry of Agriculture, Key Laboratory of Monitoring and Management of Crop Diseases and Pest Insects, Nanjing Agricultural University, Nanjing 210095, PR China; Department of Science, College of Science, Nanjing Agricultural University, Nanjing 210095, PR China.
authors.forename: Junjun
authors.initials: J
authors.lastname: Wang
authors.affiliation: Jiangsu Key Laboratory of Pesticide Science, Nanjing Agricultural, Nanjing 210095, PR China; Ministry of Agriculture, Key Laboratory of Monitoring and Management of Crop Diseases and Pest Insects, Nanjing Agricultural University, Nanjing 210095, PR China.
authors.forename: Aimin
authors.initials: A
authors.lastname: Lu
authors.affiliation: Jiangsu Key Laboratory of Pesticide Science, Nanjing Agricultural, Nanjing 210095, PR China; Ministry of Agriculture, Key Laboratory of Monitoring and Management of Crop Diseases and Pest Insects, Nanjing Agricultural University, Nanjing 210095, PR China; Department of Science, College of Science, Nanjing Agricultural University, Nanjing 210095, PR China. Electronic address: ycl@njau.edu.cn.
authors.forename: Chunlong
authors.initials: C
authors.lastname: Yang
mesh_terms: D000935:Antifungal Agents; D020171:Botrytis / Q000187:drug effects*; D004305:Dose-Response Relationship, Drug; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D015394:Molecular Structure; D010659:Phenylhydrazines / Q000737:chemistry*; D021281:Quantitative Structure-Activity Relationship
chemical_list: D000935:Antifungal Agents; D005663:Furans; D010659:Phenylhydrazines; C030299:phenylhydrazine; C003422:tetronic acid
keywords: 3D-QSAR; Antifungal activity; Substituted phenylhydrazine; Tetronic acid; X-ray diffraction