title: Synthesis and antiproliferative activity of α-branched α,β-unsaturated ketones.
abstract: A series of α-branched α,β-unsaturated ketones were prepared in a straightforward manner by the acid catalyzed coupling between arylalkynes and carbaldehydes. The method also allows producing as side product chalcone analogs bearing an additional α,β-unsaturated arylketone in the molecular scaffold. The evaluation of the antiproliferative activity in the human solid tumor cell lines HBL-100 (breast), HeLa (cervix), SW1573 (non-small cell lung), T-47D (breast) and WiDr (colon) provided a structure-activity relationship. Overall, the compounds presented active against the resistant cancer cells T-47D. The resulting lead, displaying an unprecedented chalcone scaffold, showed GI50 values in the range 0.32-0.53 μM against all cell lines tested. The methoxy group present in the lead might play an important role in the activity.
authors.affiliation: Department of Organic Chemistry, Faculty of Chemistry, Vilnius University, Naugarduko 24, Vilnius LT 03225, Lithuania.
authors.forename: Ieva
authors.initials: I
authors.lastname: Karpaviciene
authors.forename: Inga
authors.initials: I
authors.lastname: Cikotiene
authors.forename: José M
authors.initials: JM
authors.lastname: Padrón
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D049109:Cell Proliferation / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006367:HeLa Cells; D006801:Humans; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
chemical_list: D000970:Antineoplastic Agents; D007659:Ketones
keywords: Antitumor agents; Chalcones; Lewis acids; Structure–activity relationships; α-Branched α,β-unsaturated ketones