title: Natural products as sources of new fungicides (III): Antifungal activity of 2,4-dihydroxy-5-methylacetophenone derivatives.
abstract: A series of new 2,4-dihydroxy-5-methylacetophenone 2 derivatives were synthesized, and characterized by (1)H, (13)C NMR and ESI-MS. Their antifungal activities were evaluated in vitro against five important plant fungal pathogens including Cytospora sp., Glomerella cingulate, Pyricularia oryzaecar, Botrytis cinerea and Alternaria solani by the mycelial growth inhibitory rate assay. Compounds 2b-d, 2g and 2h displayed a broad-spectrum activity. The logP value of these active compounds is ranging from 1.71 to 2.54. Especially, isopropyl ketone 2g (logP 2.27) was found to be the most active to the tested organisms with IC50 values of 17.28-32.32 μg/mL. The results suggest that compound 2g might be a promising candidate in the development of new agrochemical antifungal agents. Preliminary structure-activity relationship (SAR) studies of the acetophenone derivatives are also discussed.
authors.affiliation: Shaanxi Key Labotory of Natural Products & Chemical Biology, College of Science, Northwest A&F University, Yangling 712100, People's Republic of China.
authors.forename: Wei
authors.initials: W
authors.lastname: Shi
authors.affiliation: Shaanxi Key Labotory of Natural Products & Chemical Biology, College of Science, Northwest A&F University, Yangling 712100, People's Republic of China.
authors.forename: Wen-Jia
authors.initials: WJ
authors.lastname: Dan
authors.affiliation: Shaanxi Key Labotory of Natural Products & Chemical Biology, College of Science, Northwest A&F University, Yangling 712100, People's Republic of China.
authors.forename: Jiang-Jiang
authors.initials: JJ
authors.lastname: Tang
authors.affiliation: Shaanxi Key Labotory of Natural Products & Chemical Biology, College of Science, Northwest A&F University, Yangling 712100, People's Republic of China.
authors.forename: Yan
authors.initials: Y
authors.lastname: Zhang
authors.affiliation: Shaanxi Key Labotory of Natural Products & Chemical Biology, College of Science, Northwest A&F University, Yangling 712100, People's Republic of China.
authors.forename: Tseden
authors.initials: T
authors.lastname: Nandinsuren
authors.affiliation: Shaanxi Key Labotory of Natural Products & Chemical Biology, College of Science, Northwest A&F University, Yangling 712100, People's Republic of China.
authors.forename: An-Ling
authors.initials: AL
authors.lastname: Zhang
authors.affiliation: Shaanxi Key Labotory of Natural Products & Chemical Biology, College of Science, Northwest A&F University, Yangling 712100, People's Republic of China. Electronic address: jinminggao@nwsuaf.edu.cn.
authors.forename: Jin-Ming
authors.initials: JM
authors.lastname: Gao
mesh_terms: D000098:Acetophenones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D005659:Fungicides, Industrial / Q000138:chemical synthesis / Q000737:chemistry; D020128:Inhibitory Concentration 50; D003904:Mitosporic Fungi; D020081:Phyllachorales; D013329:Structure-Activity Relationship
chemical_list: C000621248:2,4-dihydroxy-5-methylacetophenone; D000098:Acetophenones; D005659:Fungicides, Industrial
keywords: Acetophenone derivatives; Agrochemicals; Antifungal agents; Natural products; Phytopathogenic fungi; Structure–activity relationship