Aqueous synthesis of N,S-dialkylthiophosphoramidates: design, optimisation and application to library construction and antileishmanial testing
Authorized Users Only
2013
Authors
Trmčić, MilenaChadbourne, Frances L.
Brear, Paul M.
Denny, Paul W.
Cobb, Steven L.
Hodgson, David R. W.
Article (Published version)
Metadata
Show full item recordAbstract
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, 2660-2675Publisher:
- Royal Soc Chemistry, Cambridge
Funding / projects:
- Royal Society
- EPSRC
- Wolfson Small Grants Scheme
- Durham University
Note:
- Peer-reviewed manuscript: http://cherry.chem.bg.ac.rs/handle/123456789/2821
- Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3468
DOI: 10.1039/c3ob27448a
ISSN: 1477-0520
PubMed: 23467665
WoS: 000316803900016
Scopus: 2-s2.0-84876986050
Collections
Institution/Community
Inovacioni centar / Innovation CentreTY - JOUR AU - Trmčić, Milena AU - Chadbourne, Frances L. AU - Brear, Paul M. AU - Denny, Paul W. AU - Cobb, Steven L. AU - Hodgson, David R. W. PY - 2013 UR - https://cherry.chem.bg.ac.rs/handle/123456789/1620 AB - 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. PB - Royal Soc Chemistry, Cambridge T2 - Organic and Biomolecular Chemistry T1 - Aqueous synthesis of N,S-dialkylthiophosphoramidates: design, optimisation and application to library construction and antileishmanial testing VL - 11 IS - 16 SP - 2660 EP - 2675 DO - 10.1039/c3ob27448a ER -
@article{ author = "Trmčić, Milena and Chadbourne, Frances L. and Brear, Paul M. and Denny, Paul W. and Cobb, Steven L. and Hodgson, David R. W.", year = "2013", 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.", publisher = "Royal Soc Chemistry, Cambridge", journal = "Organic and Biomolecular Chemistry", title = "Aqueous synthesis of N,S-dialkylthiophosphoramidates: design, optimisation and application to library construction and antileishmanial testing", volume = "11", number = "16", pages = "2660-2675", doi = "10.1039/c3ob27448a" }
Trmčić, M., Chadbourne, F. L., Brear, P. M., Denny, P. W., Cobb, S. L.,& Hodgson, D. R. W.. (2013). Aqueous synthesis of N,S-dialkylthiophosphoramidates: design, optimisation and application to library construction and antileishmanial testing. in Organic and Biomolecular Chemistry Royal Soc Chemistry, Cambridge., 11(16), 2660-2675. https://doi.org/10.1039/c3ob27448a
Trmčić M, Chadbourne FL, Brear PM, Denny PW, Cobb SL, Hodgson DRW. Aqueous synthesis of N,S-dialkylthiophosphoramidates: design, optimisation and application to library construction and antileishmanial testing. in Organic and Biomolecular Chemistry. 2013;11(16):2660-2675. doi:10.1039/c3ob27448a .
Trmčić, Milena, Chadbourne, Frances L., Brear, Paul M., Denny, Paul W., Cobb, Steven L., Hodgson, David R. W., "Aqueous synthesis of N,S-dialkylthiophosphoramidates: design, optimisation and application to library construction and antileishmanial testing" in Organic and Biomolecular Chemistry, 11, no. 16 (2013):2660-2675, https://doi.org/10.1039/c3ob27448a . .