136258-02-1Relevant academic research and scientific papers
3,4-Dihydroxychalcones as potent 5-lipoxygenase and cyclooxygenase inhibitors
Sogawa,Nihro,Ueda,Izumi,Miki,Matsumoto,Satoh
, p. 3904 - 3909 (2007/10/02)
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.
Synthesis of 2'-hydroxychalcone epoxides
Adams,Main
, p. 4959 - 4978 (2007/10/05)
Various preparations of some 2'-tetrahydropyran-2-yloxychalcone epoxides and removal of their tetrahydropyranyl (THP) protective groups in slightly aqueous acidic dioxane are described. So synthesised were 2'-hydroxy-6'-isopropoxy- and 2'-hydroxy-6'-methoxychalcone epoxide, as well as the 2-CF3, 4-Cl and 4-NO2 analogues of the latter. 2',4'-dihydroxy-6'-methoxychalcone epoxide was similarly prepared. In some other 6'-methoxy cases protective group removal was accompanied by epoxide solvolysis and the corresponding α,β-dihydroxydihydrochalcone was the only isolable product [2-OMe, 4-OMe, 3,4,5-(OMe)3 cases] or a byproduct [4-Me case]. Similarly prepared by THP removal were 2'-hydroxy-4'-methoxychalcone epoxide and 2',4'-dihydroxychalcone epoxide, whereas an attempt to convert 2',6'-ditetrahydropyranyloxychalcone epoxide into 2',6'-dihydroxychalcone epoxide gave the product of cyclisation of the latter, 3,5-dihydroxyflavanone.
