Diaryl and Heteroaryl Sulfides: Synthesis via Sulfenyl Chlorides and Evaluation as Selective Anti-Breast-Cancer Agents

[Image: see text] A mild protocol for the synthesis of diaryl and heteroaryl sulfides is described. In a one-pot procedure, thiols are converted to sulfenyl chlorides and reacted with arylzinc reagents. This method tolerates functional groups including aryl fluorides and chlorides, ketones, as well...

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Autores principales: Yonova, Ivelina M., Osborne, Charlotte A., Morrissette, Naomi S., Jarvo, Elizabeth R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3985953/
https://www.ncbi.nlm.nih.gov/pubmed/24564865
http://dx.doi.org/10.1021/jo402586v
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author Yonova, Ivelina M.
Osborne, Charlotte A.
Morrissette, Naomi S.
Jarvo, Elizabeth R.
author_facet Yonova, Ivelina M.
Osborne, Charlotte A.
Morrissette, Naomi S.
Jarvo, Elizabeth R.
author_sort Yonova, Ivelina M.
collection PubMed
description [Image: see text] A mild protocol for the synthesis of diaryl and heteroaryl sulfides is described. In a one-pot procedure, thiols are converted to sulfenyl chlorides and reacted with arylzinc reagents. This method tolerates functional groups including aryl fluorides and chlorides, ketones, as well as N-heterocycles including pyrimidines, imidazoles, tetrazoles, and oxadiazoles. Two compounds synthesized by this method exhibited selective activity against the MCF-7 breast cancer cell line in the micromolar range.
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spelling pubmed-39859532015-02-25 Diaryl and Heteroaryl Sulfides: Synthesis via Sulfenyl Chlorides and Evaluation as Selective Anti-Breast-Cancer Agents Yonova, Ivelina M. Osborne, Charlotte A. Morrissette, Naomi S. Jarvo, Elizabeth R. J Org Chem [Image: see text] A mild protocol for the synthesis of diaryl and heteroaryl sulfides is described. In a one-pot procedure, thiols are converted to sulfenyl chlorides and reacted with arylzinc reagents. This method tolerates functional groups including aryl fluorides and chlorides, ketones, as well as N-heterocycles including pyrimidines, imidazoles, tetrazoles, and oxadiazoles. Two compounds synthesized by this method exhibited selective activity against the MCF-7 breast cancer cell line in the micromolar range. American Chemical Society 2014-02-25 2014-03-07 /pmc/articles/PMC3985953/ /pubmed/24564865 http://dx.doi.org/10.1021/jo402586v Text en Copyright © 2014 American Chemical Society
spellingShingle Yonova, Ivelina M.
Osborne, Charlotte A.
Morrissette, Naomi S.
Jarvo, Elizabeth R.
Diaryl and Heteroaryl Sulfides: Synthesis via Sulfenyl Chlorides and Evaluation as Selective Anti-Breast-Cancer Agents
title Diaryl and Heteroaryl Sulfides: Synthesis via Sulfenyl Chlorides and Evaluation as Selective Anti-Breast-Cancer Agents
title_full Diaryl and Heteroaryl Sulfides: Synthesis via Sulfenyl Chlorides and Evaluation as Selective Anti-Breast-Cancer Agents
title_fullStr Diaryl and Heteroaryl Sulfides: Synthesis via Sulfenyl Chlorides and Evaluation as Selective Anti-Breast-Cancer Agents
title_full_unstemmed Diaryl and Heteroaryl Sulfides: Synthesis via Sulfenyl Chlorides and Evaluation as Selective Anti-Breast-Cancer Agents
title_short Diaryl and Heteroaryl Sulfides: Synthesis via Sulfenyl Chlorides and Evaluation as Selective Anti-Breast-Cancer Agents
title_sort diaryl and heteroaryl sulfides: synthesis via sulfenyl chlorides and evaluation as selective anti-breast-cancer agents
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3985953/
https://www.ncbi.nlm.nih.gov/pubmed/24564865
http://dx.doi.org/10.1021/jo402586v
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AT morrissettenaomis diarylandheteroarylsulfidessynthesisviasulfenylchloridesandevaluationasselectiveantibreastcanceragents
AT jarvoelizabethr diarylandheteroarylsulfidessynthesisviasulfenylchloridesandevaluationasselectiveantibreastcanceragents

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