Synthesis of Heterocyclic Triads by Pd-Catalyzed Cross-Couplings and Evaluation of Their Cell-Specific Toxicity Profile

[Image: see text] 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 f...

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Autores principales: Salamoun, Joseph, Anderson, Shelby, Burnett, James C., Gussio, Rick, Wipf, Peter
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3983320/
https://www.ncbi.nlm.nih.gov/pubmed/24641272
http://dx.doi.org/10.1021/ol500620m
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author Salamoun, Joseph
Anderson, Shelby
Burnett, James C.
Gussio, Rick
Wipf, Peter
author_facet Salamoun, Joseph
Anderson, Shelby
Burnett, James C.
Gussio, Rick
Wipf, Peter
author_sort Salamoun, Joseph
collection PubMed
description [Image: see text] 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.
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spelling pubmed-39833202015-03-18 Synthesis of Heterocyclic Triads by Pd-Catalyzed Cross-Couplings and Evaluation of Their Cell-Specific Toxicity Profile Salamoun, Joseph Anderson, Shelby Burnett, James C. Gussio, Rick Wipf, Peter Org Lett [Image: see text] 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. American Chemical Society 2014-03-18 2014-04-04 /pmc/articles/PMC3983320/ /pubmed/24641272 http://dx.doi.org/10.1021/ol500620m Text en Copyright © 2014 American Chemical Society
spellingShingle Salamoun, Joseph
Anderson, Shelby
Burnett, James C.
Gussio, Rick
Wipf, Peter
Synthesis of Heterocyclic Triads by Pd-Catalyzed Cross-Couplings and Evaluation of Their Cell-Specific Toxicity Profile
title Synthesis of Heterocyclic Triads by Pd-Catalyzed Cross-Couplings and Evaluation of Their Cell-Specific Toxicity Profile
title_full Synthesis of Heterocyclic Triads by Pd-Catalyzed Cross-Couplings and Evaluation of Their Cell-Specific Toxicity Profile
title_fullStr Synthesis of Heterocyclic Triads by Pd-Catalyzed Cross-Couplings and Evaluation of Their Cell-Specific Toxicity Profile
title_full_unstemmed Synthesis of Heterocyclic Triads by Pd-Catalyzed Cross-Couplings and Evaluation of Their Cell-Specific Toxicity Profile
title_short Synthesis of Heterocyclic Triads by Pd-Catalyzed Cross-Couplings and Evaluation of Their Cell-Specific Toxicity Profile
title_sort synthesis of heterocyclic triads by pd-catalyzed cross-couplings and evaluation of their cell-specific toxicity profile
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3983320/
https://www.ncbi.nlm.nih.gov/pubmed/24641272
http://dx.doi.org/10.1021/ol500620m
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