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EPSRC

Authors

Publications

Aqueous synthesis of N,S-dialkylthiophosphoramidates: design, optimisation and application to library construction and antileishmanial testing

Trmčić, Milena; Chadbourne, Frances L.; Brear, Paul M.; Denny, Paul W.; Cobb, Steven L.; Hodgson, David R. W.

(Royal Soc Chemistry, Cambridge, 2013) 

TY  - 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 . .
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Aqueous synthesis of N,S-dialkylthiophosphoramidates: design, optimisation and application to library construction and antileishmanial testing

Trmčić, Milena; Chadbourne, Frances L.; Brear, Paul M.; Denny, Paul W.; Cobb, Steven L.; Hodgson, David R. W.

(Royal Soc Chemistry, Cambridge, 2013) 

TY  - 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/123456789/2821
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 . .
6
4
4
6

Supplementary data for article: Trmčić, M.; Chadbourne, F. L.; Brear, P. M.; Denny, P. W.; Cobb, S. L.; Hodgson, D. R. W. Aqueous Synthesis of N,S-Dialkylthiophosphoramidates: Design, Optimisation and Application to Library Construction and Antileishmanial Testing. Organic and Biomolecular Chemistry 2013, 11 (16), 2660–2675. https://doi.org/10.1039/c3ob27448a

Trmčić, Milena; Chadbourne, Frances L.; Brear, Paul M.; Denny, Paul W.; Cobb, Steven L.; Hodgson, David R. W.

(Royal Soc Chemistry, Cambridge, 2013) 

TY  - DATA
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/123456789/3468
PB  - Royal Soc Chemistry, Cambridge
T2  - Organic and Biomolecular Chemistry
T1  - Supplementary data for article: Trmčić, M.; Chadbourne, F. L.; Brear, P. M.; Denny, P. W.; Cobb, S. L.; Hodgson, D. R. W. Aqueous Synthesis of N,S-Dialkylthiophosphoramidates: Design, Optimisation and Application to Library Construction and Antileishmanial Testing. Organic and Biomolecular Chemistry 2013, 11 (16), 2660–2675. https://doi.org/10.1039/c3ob27448a
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3468
ER  - 
@misc{
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",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Organic and Biomolecular Chemistry",
title = "Supplementary data for article: Trmčić, M.; Chadbourne, F. L.; Brear, P. M.; Denny, P. W.; Cobb, S. L.; Hodgson, D. R. W. Aqueous Synthesis of N,S-Dialkylthiophosphoramidates: Design, Optimisation and Application to Library Construction and Antileishmanial Testing. Organic and Biomolecular Chemistry 2013, 11 (16), 2660–2675. https://doi.org/10.1039/c3ob27448a",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3468"
}
Trmčić, M., Chadbourne, F. L., Brear, P. M., Denny, P. W., Cobb, S. L.,& Hodgson, D. R. W.. (2013). Supplementary data for article: Trmčić, M.; Chadbourne, F. L.; Brear, P. M.; Denny, P. W.; Cobb, S. L.; Hodgson, D. R. W. Aqueous Synthesis of N,S-Dialkylthiophosphoramidates: Design, Optimisation and Application to Library Construction and Antileishmanial Testing. Organic and Biomolecular Chemistry 2013, 11 (16), 2660–2675. https://doi.org/10.1039/c3ob27448a. in Organic and Biomolecular Chemistry
Royal Soc Chemistry, Cambridge..
https://hdl.handle.net/21.15107/rcub_cherry_3468
Trmčić M, Chadbourne FL, Brear PM, Denny PW, Cobb SL, Hodgson DRW. Supplementary data for article: Trmčić, M.; Chadbourne, F. L.; Brear, P. M.; Denny, P. W.; Cobb, S. L.; Hodgson, D. R. W. Aqueous Synthesis of N,S-Dialkylthiophosphoramidates: Design, Optimisation and Application to Library Construction and Antileishmanial Testing. Organic and Biomolecular Chemistry 2013, 11 (16), 2660–2675. https://doi.org/10.1039/c3ob27448a. in Organic and Biomolecular Chemistry. 2013;.
https://hdl.handle.net/21.15107/rcub_cherry_3468 .
Trmčić, Milena, Chadbourne, Frances L., Brear, Paul M., Denny, Paul W., Cobb, Steven L., Hodgson, David R. W., "Supplementary data for article: Trmčić, M.; Chadbourne, F. L.; Brear, P. M.; Denny, P. W.; Cobb, S. L.; Hodgson, D. R. W. Aqueous Synthesis of N,S-Dialkylthiophosphoramidates: Design, Optimisation and Application to Library Construction and Antileishmanial Testing. Organic and Biomolecular Chemistry 2013, 11 (16), 2660–2675. https://doi.org/10.1039/c3ob27448a" in Organic and Biomolecular Chemistry (2013),
https://hdl.handle.net/21.15107/rcub_cherry_3468 .