title: Efficient synthesis and anti-fungal activity of oleanolic acid oxime esters.
abstract: In order to develop potential glucosamine-6-phosphate synthase inhibitors and anti-fungal agents, twenty five oleanolic acid oxime esters were synthesized in an efficient way. The structures of the new compounds were confirmed by MS, HRMS, 1H-NMR and 13C-NMR. Preliminary studies based on means of the Elson-Morgan method indicated that many compounds exhibited some inhibitory activity of glucosamine-6-phosphate synthase (GlmS), and the original fungicidal activities results showed that some of the compounds exhibited good fungicidal activities towards Sclerotinia sclerotiorum (Lib.) de Bary, Rhizoctonia solani Kuhn and Botrytis cinerea Pers at the concentration of 50 µg/mL. These compounds would thus merit further study and development as antifungal agents.
authors.affiliation: Department of Applied Chemistry, China Agricultural University, Beijing 100193, China.
authors.forename: Hanqing
authors.initials: H
authors.lastname: Zhao
authors.forename: Minjie
authors.initials: M
authors.lastname: Zhou
authors.forename: Lifeng
authors.initials: L
authors.lastname: Duan
authors.forename: Wei
authors.initials: W
authors.lastname: Wang
authors.forename: Jianjun
authors.initials: J
authors.lastname: Zhang
authors.forename: Daoquan
authors.initials: D
authors.lastname: Wang
authors.forename: Xiaomei
authors.initials: X
authors.lastname: Liang
mesh_terms: D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001203:Ascomycota / Q000187:drug effects; D020171:Botrytis / Q000187:drug effects; D002176:Candida albicans / Q000201:enzymology; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D004952:Esters; D005656:Fungal Proteins / Q000037:antagonists & inhibitors / Q000737:chemistry; D005659:Fungicides, Industrial / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D005670:Fusarium / Q000187:drug effects; D005945:Glutamine-Fructose-6-Phosphate Transaminase (Isomerizing) / Q000037:antagonists & inhibitors / Q000737:chemistry; D008826:Microbial Sensitivity Tests; D009828:Oleanolic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D010091:Oximes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D010838:Phytophthora / Q000187:drug effects; D010935:Plant Diseases / Q000382:microbiology
chemical_list: D000935:Antifungal Agents; D004791:Enzyme Inhibitors; D004952:Esters; D005656:Fungal Proteins; D005659:Fungicides, Industrial; D010091:Oximes; D009828:Oleanolic Acid; D005945:Glutamine-Fructose-6-Phosphate Transaminase (Isomerizing)