Ene Reaction of Nitrosocarbonyl Mesitylene with the Cinnamyl Alcohol: Metabolic Activity and Apoptosis of the Synthetized 6-Chloropurine N,O-Nucleoside Analogues

[Image: see text] Nitrosocarbonyl mesitylene intermediate undergoes an ene reaction with cinnamyl alcohol affording the corresponding 5-hydroxy-isoxazolidine in fair yields. The synthesized 5-acetoxy-isoxazolidine serves as synthon for the preparation of 6-chloropurine N,O-nucleoside analogues, acco...

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Autores principales: Memeo, Misal Giuseppe, Valletta, Elena, Macchi, Beatrice, Porta, Alessio, Bovio, Bruna, Moiola, Mattia, Quadrelli, Paolo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2018
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6068682/
https://www.ncbi.nlm.nih.gov/pubmed/30087920
http://dx.doi.org/10.1021/acsomega.8b00970
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author Memeo, Misal Giuseppe
Valletta, Elena
Macchi, Beatrice
Porta, Alessio
Bovio, Bruna
Moiola, Mattia
Quadrelli, Paolo
author_facet Memeo, Misal Giuseppe
Valletta, Elena
Macchi, Beatrice
Porta, Alessio
Bovio, Bruna
Moiola, Mattia
Quadrelli, Paolo
author_sort Memeo, Misal Giuseppe
collection PubMed
description [Image: see text] Nitrosocarbonyl mesitylene intermediate undergoes an ene reaction with cinnamyl alcohol affording the corresponding 5-hydroxy-isoxazolidine in fair yields. The synthesized 5-acetoxy-isoxazolidine serves as synthon for the preparation of 6-chloropurine N,O-nucleoside analogues, according to the Vorbrüggen reaction. The compounds were evaluated for their metabolic and apoptotic activity, and their structure–activity relationship is discussed.
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spelling pubmed-60686822018-08-05 Ene Reaction of Nitrosocarbonyl Mesitylene with the Cinnamyl Alcohol: Metabolic Activity and Apoptosis of the Synthetized 6-Chloropurine N,O-Nucleoside Analogues Memeo, Misal Giuseppe Valletta, Elena Macchi, Beatrice Porta, Alessio Bovio, Bruna Moiola, Mattia Quadrelli, Paolo ACS Omega [Image: see text] Nitrosocarbonyl mesitylene intermediate undergoes an ene reaction with cinnamyl alcohol affording the corresponding 5-hydroxy-isoxazolidine in fair yields. The synthesized 5-acetoxy-isoxazolidine serves as synthon for the preparation of 6-chloropurine N,O-nucleoside analogues, according to the Vorbrüggen reaction. The compounds were evaluated for their metabolic and apoptotic activity, and their structure–activity relationship is discussed. American Chemical Society 2018-07-10 /pmc/articles/PMC6068682/ /pubmed/30087920 http://dx.doi.org/10.1021/acsomega.8b00970 Text en Copyright © 2018 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Memeo, Misal Giuseppe
Valletta, Elena
Macchi, Beatrice
Porta, Alessio
Bovio, Bruna
Moiola, Mattia
Quadrelli, Paolo
Ene Reaction of Nitrosocarbonyl Mesitylene with the Cinnamyl Alcohol: Metabolic Activity and Apoptosis of the Synthetized 6-Chloropurine N,O-Nucleoside Analogues
title Ene Reaction of Nitrosocarbonyl Mesitylene with the Cinnamyl Alcohol: Metabolic Activity and Apoptosis of the Synthetized 6-Chloropurine N,O-Nucleoside Analogues
title_full Ene Reaction of Nitrosocarbonyl Mesitylene with the Cinnamyl Alcohol: Metabolic Activity and Apoptosis of the Synthetized 6-Chloropurine N,O-Nucleoside Analogues
title_fullStr Ene Reaction of Nitrosocarbonyl Mesitylene with the Cinnamyl Alcohol: Metabolic Activity and Apoptosis of the Synthetized 6-Chloropurine N,O-Nucleoside Analogues
title_full_unstemmed Ene Reaction of Nitrosocarbonyl Mesitylene with the Cinnamyl Alcohol: Metabolic Activity and Apoptosis of the Synthetized 6-Chloropurine N,O-Nucleoside Analogues
title_short Ene Reaction of Nitrosocarbonyl Mesitylene with the Cinnamyl Alcohol: Metabolic Activity and Apoptosis of the Synthetized 6-Chloropurine N,O-Nucleoside Analogues
title_sort ene reaction of nitrosocarbonyl mesitylene with the cinnamyl alcohol: metabolic activity and apoptosis of the synthetized 6-chloropurine n,o-nucleoside analogues
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6068682/
https://www.ncbi.nlm.nih.gov/pubmed/30087920
http://dx.doi.org/10.1021/acsomega.8b00970
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