M. Trmčić
Aqueous synthesis of N,S,-dialkylthiophosphoramidates: design, optimisation and application to library construction and antileishmanial testing
Trmčić, M.; Chadbourne, F.L.; Brear, P.M.; Denny, P.W.; Cobb, S.L.; Hodgson, D.R.W.
Authors
F.L. Chadbourne
P.M. Brear
Professor Paul Denny p.w.denny@durham.ac.uk
Professor
Professor Steven Cobb s.l.cobb@durham.ac.uk
Professor
Professor David Hodgson d.r.w.hodgson@durham.ac.uk
Professor
Abstract
We recently reported the use of PSCl3 for the thiophosphorylation of alkylamines where the resulting N-thiophosphoramidate ions could be readily S-alkylated (Chem. Commun., 2011, 47, 6156–6158.). Herein we report the development of this methodology using amino acid, amino sugar, aminonucleoside and aniline substrates. The hydrolysis properties of N-thiophosphoramidate ions and their reactivities towards alkylating agents are also explored. In addition, we demonstrate the application of our approach to the preparation of a small library of compounds, including quinoline-based N,S-dialkylthiophosphoramidates which were tested for antileishmanial activity.
Citation
Trmčić, M., Chadbourne, F., Brear, P., Denny, P., Cobb, S., & Hodgson, D. (2013). Aqueous synthesis of N,S,-dialkylthiophosphoramidates: design, optimisation and application to library construction and antileishmanial testing. Organic and Biomolecular Chemistry, 11(16), 2660-2675. https://doi.org/10.1039/c3ob27448a
Journal Article Type | Article |
---|---|
Publication Date | Jan 1, 2013 |
Deposit Date | Feb 28, 2013 |
Publicly Available Date | May 9, 2013 |
Journal | Organic and Biomolecular Chemistry |
Print ISSN | 1477-0520 |
Electronic ISSN | 1477-0539 |
Publisher | Royal Society of Chemistry |
Peer Reviewed | Peer Reviewed |
Volume | 11 |
Issue | 16 |
Pages | 2660-2675 |
DOI | https://doi.org/10.1039/c3ob27448a |
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