Stability studies of oxazolidine-based compounds using 1H NMR spectroscopy

Moloney, Gerard P., Iskander, Magdy N. and Craik, David J. (2010) Stability studies of oxazolidine-based compounds using 1H NMR spectroscopy. Journal of Pharmaceutical Sciences, 99 8: 3362-3371. doi:10.1002/jps.22108

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Author Moloney, Gerard P.
Iskander, Magdy N.
Craik, David J.
Title Stability studies of oxazolidine-based compounds using 1H NMR spectroscopy
Journal name Journal of Pharmaceutical Sciences   Check publisher's open access policy
ISSN 0022-3549
Publication date 2010-08
Sub-type Article (original research)
DOI 10.1002/jps.22108
Volume 99
Issue 8
Start page 3362
End page 3371
Total pages 10
Editor Ronald T. Borchardt
Place of publication Hoboken, NJ
Publisher Wiley-Liss
Collection year 2011
Language eng
Formatted abstract
A series of oxazolidine-based compounds with a variety of substituents in positions 2 and 3 was synthesized and their stability studied. Ring opened intermediates formed on addition of limiting amounts of D2O to oxazolidine solutions, as observed by NMR. As the hydrolysis reactions proceeded, a series of novel dimeric β-amino alcohol compounds formed via an internal reaction between ephedrine and the ring opened intermediates. 2-Phenyl substituted oxazolidine compounds containing electron withdrawing nitro substituents were more rapidly hydrolyzed than the unsubstituted derivative and methoxy substituted compounds, with the nitro substituents appearing to stabilize the ring opened intermediates. Two oxazolidine derivatives, with a methyl and proton at position 2, were found to be more stable to oxazolidine hydrolysis than the 2-phenyl substituted compounds. Oxazolidines incorporating phenyl substituents at position 3 were synthesized and found to be less stable than those incorporating a methyl substituent at position 3. These fundamental structure–activity relationships may be useful when choosing oxazolidine derivatives as synthetic intermediates and as prodrugs for the delivery of compounds containing either β-amino alcohol or aldehyde components.
© 2010 Wiley-Liss, Inc. and the American Pharmacists Association
Keyword NMR spectroscopy
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2011 Collection
Institute for Molecular Bioscience - Publications
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Citation counts: TR Web of Science Citation Count  Cited 4 times in Thomson Reuters Web of Science Article | Citations
Scopus Citation Count Cited 3 times in Scopus Article | Citations
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Created: Sun, 15 Aug 2010, 00:03:25 EST