title: Synthesis and anti-inflammatory activities of novel dihydropyranoaurone derivatives.
abstract: A novel series of dihydropyranoaurone derivatives were synthesized and evaluated as potential anti-inflammatory agents. Late-stage derivatization by versatile piperazine-catalyzed aldol reaction between dihydropyanobenzofuran intermediate 2 and diverse aldehydes readily afforded the novel dihydropyranoaurone analogs. Evaluation of the synthesized dihydropyranoaurone derivatives and related compounds regarding their inhibiting inducible nitric oxide synthase and nitrite production of lipopolysaccaride-stimulated RAW 264.7 cells provided insight into the structure-activity relationship of aurone derivatives.
authors.affiliation: College of Pharmacy, Woosuk University, Wanju, 55338, Korea.
authors.forename: Zheng
authors.initials: Z
authors.lastname: Wang
authors.affiliation: College of Pharmacy, Woosuk University, Wanju, 55338, Korea. ejbae@woosuk.ac.kr.
authors.forename: Eun Ju
authors.initials: EJ
authors.lastname: Bae
authors.affiliation: College of Pharmacy, Dankook University, Cheonan, 31116, Korea. hanyt@dankook.ac.kr.
authors.forename: Young Taek
authors.initials: YT
authors.lastname: Han
mesh_terms: D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001572:Benzofurans / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002470:Cell Survival / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D008070:Lipopolysaccharides / Q000037:antagonists & inhibitors / Q000494:pharmacology; D008264:Macrophages / Q000187:drug effects / Q000378:metabolism; D051379:Mice; D015394:Molecular Structure; D052247:Nitric Oxide Synthase Type II / Q000037:antagonists & inhibitors* / Q000378:metabolism; D009573:Nitrites / Q000037:antagonists & inhibitors* / Q000378:metabolism; D000067996:RAW 264.7 Cells; D013329:Structure-Activity Relationship
chemical_list: D000894:Anti-Inflammatory Agents, Non-Steroidal; D001572:Benzofurans; D004791:Enzyme Inhibitors; D008070:Lipopolysaccharides; D009573:Nitrites; C486837:aurone; D052247:Nitric Oxide Synthase Type II
keywords: Aldol reaction; Anti-inflammation; Dihydropyranoaurone; Late-stage derivatization; Nitric oxide; Synthesis