Aqueous synthesis of N,S-dialkylthiophosphoramidates: design, optimisation and application to library construction and antileishmanial testing
Chadbourne, Frances L.
Brear, Paul M.
Denny, Paul W.
Cobb, Steven L.
Hodgson, David R. W.
Article (Accepted Version)
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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.
Source:Organic and Biomolecular Chemistry, 2013, 11, 16, 2660-2675
- Royal Soc Chemistry, Cambridge
- Royal Society
- Wolfson Small Grants Scheme
- Durham University
- This is the peer-reviewed version of the following article: Trmcic, M. and Chadbourne, F.L. and Brear, P.M. and Denny, P.W. and Cobb, S.L. and Hodgson, D.R.W., 2013. Aqueous synthesis of N,S,-dialkylthiophosphoramidates: design, optimisation and application to library construction and antileishmanial testing. Organic and biomolecular chemistry. 11, 2660-2675. http://doi.org/10.1039/c3ob27448a
- Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3468