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Aqueous synthesis of N,S-dialkylthiophosphoramidates: design, optimisation and application to library construction and antileishmanial testing
dc.creator | Trmčić, Milena | |
dc.creator | Chadbourne, Frances L. | |
dc.creator | Brear, Paul M. | |
dc.creator | Denny, Paul W. | |
dc.creator | Cobb, Steven L. | |
dc.creator | Hodgson, David R. W. | |
dc.date.accessioned | 2019-02-04T12:11:50Z | |
dc.date.available | 2014-02-28 | |
dc.date.issued | 2013 | |
dc.identifier.issn | 1477-0520 | |
dc.identifier.uri | https://cherry.chem.bg.ac.rs/handle/123456789/2821 | |
dc.description.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. | en |
dc.publisher | Royal Soc Chemistry, Cambridge | |
dc.relation | Royal Society | |
dc.relation | EPSRC | |
dc.relation | Wolfson Small Grants Scheme | |
dc.relation | Durham University | |
dc.rights | embargoedAccess | |
dc.rights.uri | https://creativecommons.org/licenses/by-nc-nd/4.0/ | |
dc.source | Organic and Biomolecular Chemistry | |
dc.title | Aqueous synthesis of N,S-dialkylthiophosphoramidates: design, optimisation and application to library construction and antileishmanial testing | en |
dc.type | article | |
dc.rights.license | BY-NC-ND | |
dcterms.abstract | Трмчић, Милена; Цхадбоурне, Францес Л.; Деннy, Паул W.; Цобб, Стевен Л.; Ходгсон, Давид Р. W.; Бреар, Паул М.; | |
dc.citation.volume | 11 | |
dc.citation.issue | 16 | |
dc.citation.spage | 2660 | |
dc.citation.epage | 2675 | |
dc.identifier.wos | 000316803900016 | |
dc.identifier.doi | 10.1039/c3ob27448a | |
dc.citation.other | 11(16): 2660-2675 | |
dc.citation.rank | M21 | |
dc.identifier.pmid | 23467665 | |
dc.description.other | 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] | |
dc.description.other | Supplementary material: [http://cherry.chem.bg.ac.rs/handle/123456789/3468] | |
dc.type.version | acceptedVersion | en |
dc.identifier.scopus | 2-s2.0-84876986050 | |
dc.identifier.fulltext | https://cherry.chem.bg.ac.rs/bitstream/id/6490/10791.pdf |