Aqueous synthesis of N,S-dialkylthiophosphoramidates: design, optimisation and application to library construction and antileishmanial testing
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Chadbourne, Frances L.
Brear, Paul M.
Denny, Paul W.
Cobb, Steven L.
Hodgson, David R. W.
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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.
Извор:Organic and Biomolecular Chemistry, 2013, 11, 16, 2660-2675
- Royal Soc Chemistry, Cambridge
- Royal Society
- Wolfson Small Grants Scheme
- Durham University
- Peer-reviewed manuscript: http://cherry.chem.bg.ac.rs/handle/123456789/2821