Aqueous synthesis of N,S-dialkylthiophosphoramidates: design, optimisation and application to library construction and antileishmanial testing
2013
Аутори
Trmčić, MilenaChadbourne, Frances L.
Brear, Paul M.
Denny, Paul W.
Cobb, Steven L.
Hodgson, David R. W.
Чланак у часопису (Рецензирана верзија)
Метаподаци
Приказ свих података о документуАпстракт
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, 2660-2675Издавач:
- Royal Soc Chemistry, Cambridge
Финансирање / пројекти:
- Royal Society
- EPSRC
- Wolfson Small Grants Scheme
- Durham University
Напомена:
- 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
DOI: 10.1039/c3ob27448a
ISSN: 1477-0520
PubMed: 23467665
WoS: 000316803900016
Scopus: 2-s2.0-84876986050
Колекције
Институција/група
Hemijski fakultet / Faculty of ChemistryTY - 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 . .