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.
Publication types
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Research Support, N.I.H., Extramural
MeSH terms
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Antineoplastic Agents / chemical synthesis*
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Antineoplastic Agents / chemistry
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Antineoplastic Agents / toxicity
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Boronic Acids / chemistry
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Catalysis
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Chemistry, Organic / methods
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Drug Screening Assays, Antitumor
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Furans / chemistry
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Heterocyclic Compounds / chemical synthesis*
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Heterocyclic Compounds / chemistry*
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Heterocyclic Compounds / toxicity
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Humans
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Molecular Structure
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Oxazoles / chemistry
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Palladium / chemistry*
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Structure-Activity Relationship
Substances
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Antineoplastic Agents
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Boronic Acids
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Furans
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Heterocyclic Compounds
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Oxazoles
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Palladium
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furan