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oai:ebyu-rdlopen.rawdatalibrary.net:ebyu/137232026-10-18T21:13:30Zopenairedrivercom_ebyu_10000col_ebyu_10001

Synthesis, biological evaluation and molecular docking studies of bis-chalcone derivatives as xanthine oxidase inhibitors and anticancer agentsBurmaoglu, SerdarOzcan, S.Balcioglu, S.Gencel, M.Noma, Samir Abbas AliEssiz, SebnemAtes, BurhanAlgul, OztekinBis-chalconeClaisen-Schmidt condensationCytotoxicityInhibitionSynthesisAntineoplastic AgentsBreast NeoplasmsCatalytic DomainCell ProliferationCell SurvivalChalconeEnzyme InhibitorsFemaleHumansMolecular Docking SimulationMolecular StructureStructure-Activity RelationshipTumor Cells, CulturedXanthine Oxidase1,1' (2 hydroxy 4,6 dimethoxy 1,3 phenylene)bis(3 phenylprop 2 en 1 one)1,1' (2 hydroxy 4,6 dimethoxy 1,3 phenylene)bis[3 (2 fluorophenyl)prop 2 en 1 one]1,1' (2 hydroxy 4,6 dimethoxy 1,3 phenylene)bis[3 (2,3 difluorophenyl)prop 2 en 1 one]1,1' (2 hydroxy 4,6 dimethoxy 1,3 phenylene)bis[3 (2,4 difluorophenyl)prop 2 en 1 one]1,1' (2 hydroxy 4,6 dimethoxy 1,3 phenylene)bis[3 (2,5 difluorophenyl)prop 2 en 1 one]1,1' (2 hydroxy 4,6 dimethoxy 1,3 phenylene)bis[3 (3 fluorophenyl)prop 2 en 1 one]1,1' (2 hydroxy 4,6 dimethoxy 1,3 phenylene)bis[3 (3,4 difluorophenyl)prop 2 en 1 one]1,1' (2 hydroxy 4,6 dimethoxy 1,3 phenylene)bis[3 (4 fluorophenyl)prop 2 en 1 one]allopurinolantineoplastic agentchalcone derivativeIn this study, a series of B-ring fluoro substituted bis-chalcone derivatives were synthesized by Claisen-Schmidt condensation reactions and evaluated for their ability to inhibit xanthine oxidase (XO) and growth inhibitory activity against MCF-7 and Caco-2 human cancer cell lines, in vitro. According to the results obtained, the bis-chalcone with fluoro group at the 2 (4b) or 2,5-position (4g) of B-ring were found to be potent inhibitors of the enzyme with IC50 values in the low micromolar range. The effects of these compounds were about 7 fold higher than allopurinol. The binding modes of the bis-chalcone derivatives in the active site of xanthine oxidase were explained using molecular docking calculations. Also, compound 4g and 4h showed in vitro growth inhibitory activity against a panel of two human cancer cell lines 1.9 and 6.8 μM of IC50 values, respectively. © 2019Academic Press Inc.2019Articlehttps://rdlopen.rawdatalibrary.net/r/ebyu/13723https://doi.org/10.1016/j.bioorg.2019.1031490045-2068enBioorganic Chemistryinfo:eu-repo/semantics/openAccessinfo:eu-repo/semantics/articlehttps://ebyu-rdlopen.rawdatalibrary.net/tr/items/ebyu/13723