title: 3,4-Dihydroxychalcones as potent 5-lipoxygenase and cyclooxygenase inhibitors.
abstract: A novel series of 3,4-dihydroxychalcones was synthesized to evaluate their effects against 5-lipoxygenase and cyclooxygenase. Almost all compounds exhibited potent inhibitory effects on 5-lipoxygenase with antioxidative effects, and some also inhibited cyclooxygenase. The 2',5'-disubstituted 3,4-dihydroxychalcones with hydroxy or alkoxy groups exhibited optimal inhibition of cyclooxygenase. We found that 2',5'-dimethoxy-3,4-dihydroxychalcone (37; HX-0836) inhibited cyclooxygenase to the same degree as flufenamic acid and 5-lipoxygenase, more than quercetin. Finally, these active inhibitors of 5-lipoxygenase inhibited arachidonic acid-induced mouse ear edema more than phenidone.
authors.affiliation: Faculty of Pharmaceutical Science, Tokushima Bunri University, Japan.
authors.forename: S
authors.initials: S
authors.lastname: Sogawa
authors.forename: Y
authors.initials: Y
authors.lastname: Nihro
authors.forename: H
authors.initials: H
authors.lastname: Ueda
authors.forename: A
authors.initials: A
authors.lastname: Izumi
authors.forename: T
authors.initials: T
authors.lastname: Miki
authors.forename: H
authors.initials: H
authors.lastname: Matsumoto
authors.forename: T
authors.initials: T
authors.lastname: Satoh
mesh_terms: D000287:Administration, Topical; D000818:Animals; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis* / Q000627:therapeutic use; D016718:Arachidonic Acid; D002460:Cell Line; D002599:Chalcone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology / Q000627:therapeutic use; D047188:Chalcones; D016861:Cyclooxygenase Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D004487:Edema / Q000139:chemically induced / Q000188:drug therapy; D015227:Lipid Peroxidation / Q000187:drug effects; D016859:Lipoxygenase Inhibitors; D008297:Male; D051379:Mice; D008813:Mice, Inbred ICR; D015394:Molecular Structure; D012756:Sheep; D013329:Structure-Activity Relationship
chemical_list: D000893:Anti-Inflammatory Agents; D047188:Chalcones; D016861:Cyclooxygenase Inhibitors; D016859:Lipoxygenase Inhibitors; C084678:2',5'-dimethoxy-3,4-dihydroxychalcone; D016718:Arachidonic Acid; D002599:Chalcone