title: Synthesis of heterocyclic triads by Pd-catalyzed cross-couplings and evaluation of their cell-specific toxicity profile.
abstract: Two complementary approaches for the preparation of linked 5-membered heterocycles were developed. The Pd-catalyzed Suzuki-Miyaura cross-coupling with halogenated furan, thiophene, and selenophene led to higher overall yields, but C,H-bond activation was a more efficient strategy for the coupling at C(2) of oxazoles. Potency and selectivity of the final hydroxymethyl products in renal (A498), lung (NCI-H226), kidney (CAKI-1), and breast (MDA-MB-468, MCF7) carcinoma cell lines were determined.
authors.affiliation: Department of Chemistry, University of Pittsburgh , Pittsburgh, Pennsylvania 15260, United States.
authors.forename: Joseph
authors.initials: J
authors.lastname: Salamoun
authors.forename: Shelby
authors.initials: S
authors.lastname: Anderson
authors.forename: James C
authors.initials: JC
authors.lastname: Burnett
authors.forename: Rick
authors.initials: R
authors.lastname: Gussio
authors.forename: Peter
authors.initials: P
authors.lastname: Wipf
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D001897:Boronic Acids / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D004354:Drug Screening Assays, Antitumor; D005663:Furans / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry* / Q000633:toxicity; D006801:Humans; D015394:Molecular Structure; D010080:Oxazoles / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D001897:Boronic Acids; D005663:Furans; D006571:Heterocyclic Compounds; D010080:Oxazoles; D010165:Palladium; C039281:furan