title: Synthesis, anti-tobacco mosaic virus and cucumber mosaic virus activity, and 3D-QSAR study of novel 1,4-pentadien-3-one derivatives containing 4-thioquinazoline moiety.
abstract: A series of novel 1,4-pentadien-3-one derivatives containing 4-thioquinazoline moiety were designed and synthesized. Antiviral bioassay results indicated that most of the title compounds exhibited excellent antiviral activities against tobacco mosaic virus (TMV) and cucumber mosaic virus (CMV) in vivo. Among the title compounds, 7j exhibited the best curative activity against TMV, with a half-maximal effective concentration (EC50) value of 213.5 μg/mL, which was better than that of ningnanmycin (270.9 μg/mL). Meanwhile, 7a showed remarkable protection activity against TMV and curative activity against CMV, with EC50 values of 124.3 and 365.5 μg/mL, respectively, which were superior to those of ningnanmycin (195.1 and 404.9 μg/mL, respectively). Comparative molecular field analysis (CoMFA) and comparative molecular similarity index analysis (CoMSIA) models were generated on the basis of the curative activities against TMV and exhibited good predictive abilities with cross-validated q(2) and non-cross-validated r(2) values for CoMFA and CoMSIA of 0.548, 0.647 and 0.994, 0.993, respectively. These results provided a practical tool for guiding the design and synthesis of novel and more potent 1,4-pentadien-3-one derivatives containing 4-thioquinazoline moiety.
authors: State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, PR China.
authors: Chengwen
authors: C
authors: Long
authors: State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, PR China.
authors: Pei
authors: P
authors: Li
authors: State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, PR China.
authors: Meihang
authors: M
authors: Chen
authors: State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, PR China.
authors: Liangrun
authors: L
authors: Dong
authors: State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, PR China. Electronic address: fcc.dyhu@gzu.edu.cn.
authors: Deyu
authors: D
authors: Hu
authors: State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, PR China. Electronic address: songbaoan22@yahoo.com.
authors: Baoan
authors: B
authors: Song
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D017799:Cucumovirus / Q000187:drug effects*; D004305:Dose-Response Relationship, Drug; D015195:Drug Design; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D010422:Pentanones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D021281:Quantitative Structure-Activity Relationship; D011799:Quinazolines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D014027:Tobacco Mosaic Virus / Q000187:drug effects*
chemical_list: D000998:Antiviral Agents; D010422:Pentanones; D011799:Quinazolines
keywords: 1,4-Pentadien-3-one; 3D-QSAR; 4-Thioquinazoline; Antiviral activity