Enantiomerically Pure Phosphonated Carbocyclic 2'-Oxa-3'-Azanucleosides: Synthesis and Biological Evaluation

Starting from enantiomeric pure 1-[(3S,5R)- and 1-[(3R,5S)-3-(hydroxymethyl)-2-methylisoxazolidin-5-yl]-5-methylpyrimidine-2,4(1H,3H)-diones (−)7a and (+)7b, obtained by lipase-catalyzed resolution, pure diethyl{[(3S,5R)-2-methyl-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)isoxazolidin-3-yl]...

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Autores principales: Romeo, Roberto, Carnovale, Caterina, Giofrè, Salvatore V., Monciino, Giulia, Chiacchio, Maria A., Sanfilippo, Claudia, Macchi, Beatrice
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2014
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6270948/
https://www.ncbi.nlm.nih.gov/pubmed/25221866
http://dx.doi.org/10.3390/molecules190914406
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author Romeo, Roberto
Carnovale, Caterina
Giofrè, Salvatore V.
Monciino, Giulia
Chiacchio, Maria A.
Sanfilippo, Claudia
Macchi, Beatrice
author_facet Romeo, Roberto
Carnovale, Caterina
Giofrè, Salvatore V.
Monciino, Giulia
Chiacchio, Maria A.
Sanfilippo, Claudia
Macchi, Beatrice
author_sort Romeo, Roberto
collection PubMed
description Starting from enantiomeric pure 1-[(3S,5R)- and 1-[(3R,5S)-3-(hydroxymethyl)-2-methylisoxazolidin-5-yl]-5-methylpyrimidine-2,4(1H,3H)-diones (−)7a and (+)7b, obtained by lipase-catalyzed resolution, pure diethyl{[(3S,5R)-2-methyl-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)isoxazolidin-3-yl]methyl}phosphonate (−)12a and diethyl{[(3R,5S)-2-methyl-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)isoxazolidin-3-yl]methyl}phosphonate (+)12b have been synthesized. The obtained compounds showed no cytotoxic activity versus the U937 cell line in comparison with AZT, and were poorly able to inhibit HIV infection in vitro.
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spelling pubmed-62709482018-12-27 Enantiomerically Pure Phosphonated Carbocyclic 2'-Oxa-3'-Azanucleosides: Synthesis and Biological Evaluation Romeo, Roberto Carnovale, Caterina Giofrè, Salvatore V. Monciino, Giulia Chiacchio, Maria A. Sanfilippo, Claudia Macchi, Beatrice Molecules Article Starting from enantiomeric pure 1-[(3S,5R)- and 1-[(3R,5S)-3-(hydroxymethyl)-2-methylisoxazolidin-5-yl]-5-methylpyrimidine-2,4(1H,3H)-diones (−)7a and (+)7b, obtained by lipase-catalyzed resolution, pure diethyl{[(3S,5R)-2-methyl-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)isoxazolidin-3-yl]methyl}phosphonate (−)12a and diethyl{[(3R,5S)-2-methyl-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)isoxazolidin-3-yl]methyl}phosphonate (+)12b have been synthesized. The obtained compounds showed no cytotoxic activity versus the U937 cell line in comparison with AZT, and were poorly able to inhibit HIV infection in vitro. MDPI 2014-09-12 /pmc/articles/PMC6270948/ /pubmed/25221866 http://dx.doi.org/10.3390/molecules190914406 Text en © 2014 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Romeo, Roberto
Carnovale, Caterina
Giofrè, Salvatore V.
Monciino, Giulia
Chiacchio, Maria A.
Sanfilippo, Claudia
Macchi, Beatrice
Enantiomerically Pure Phosphonated Carbocyclic 2'-Oxa-3'-Azanucleosides: Synthesis and Biological Evaluation
title Enantiomerically Pure Phosphonated Carbocyclic 2'-Oxa-3'-Azanucleosides: Synthesis and Biological Evaluation
title_full Enantiomerically Pure Phosphonated Carbocyclic 2'-Oxa-3'-Azanucleosides: Synthesis and Biological Evaluation
title_fullStr Enantiomerically Pure Phosphonated Carbocyclic 2'-Oxa-3'-Azanucleosides: Synthesis and Biological Evaluation
title_full_unstemmed Enantiomerically Pure Phosphonated Carbocyclic 2'-Oxa-3'-Azanucleosides: Synthesis and Biological Evaluation
title_short Enantiomerically Pure Phosphonated Carbocyclic 2'-Oxa-3'-Azanucleosides: Synthesis and Biological Evaluation
title_sort enantiomerically pure phosphonated carbocyclic 2'-oxa-3'-azanucleosides: synthesis and biological evaluation
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6270948/
https://www.ncbi.nlm.nih.gov/pubmed/25221866
http://dx.doi.org/10.3390/molecules190914406
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