Next Article in Journal
Enzyme Molecules in Solitary Confinement
Next Article in Special Issue
Unusual Structure-Energy Correlations in Intramolecular Diels–Alder Reaction Transition States
Previous Article in Journal
Identification, Characterization, and Immobilization of an Organic Solvent-Stable Alkaline Hydrolase (PA27) from Pseudomonas aeruginosa MH38
Previous Article in Special Issue
Synthesis with Perfect Atom Economy: Generation of Furan Derivatives by 1,3-Dipolar Cycloaddition of Acetylenedicarboxylates at Cyclooctynes
Article Menu

Export Article

Open AccessArticle
Molecules 2014, 19(9), 14406-14416;

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

Dipartimento Scienze del Farmaco e Prodotti per la Salute, Università di Messina, Via S.S. Annunziata, 98168 Messina, Italy
Dipartimento Scienze del Farmaco, Università di Catania, Viale A. Doria 6, 95125 Catania, Italy
Istituto di Chimica Biomolecolare del CNR, Via P. Gaifami 18, 95126 Catania, Italy
Dipartimento di Medicina dei Sistemi, Università di Roma "Tor Vergata", 00133 Roma, Italy
These authors contributed equally to this work.
Authors to whom correspondence should be addressed.
Received: 30 July 2014 / Revised: 26 August 2014 / Accepted: 29 August 2014 / Published: 12 September 2014
(This article belongs to the Special Issue Cycloaddition Chemistry)
Full-Text   |   PDF [781 KB, uploaded 12 September 2014]   |  


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. View Full-Text
Keywords: PCOANs; N,O-modified nucleosides; antiretroviral PCOANs; N,O-modified nucleosides; antiretroviral

Figure 1

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Share & Cite This Article

MDPI and ACS Style

Romeo, R.; Carnovale, C.; Giofrè, S.V.; Monciino, G.; Chiacchio, M.A.; Sanfilippo, C.; Macchi, B. Enantiomerically Pure Phosphonated Carbocyclic 2'-Oxa-3'-Azanucleosides: Synthesis and Biological Evaluation. Molecules 2014, 19, 14406-14416.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics



[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top