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Soc."},{"key":"10.1016\/j.ejmech.2018.12.038_bib60","doi-asserted-by":"crossref","first-page":"496","DOI":"10.2174\/157017809789124821","article-title":"A\u00a0new, efficient entry to non-lipophilic H-phosphonate monoesters \u2013 preparation of anti-HIV nucleotide analogues","volume":"6","author":"Romanowska","year":"2009","journal-title":"Lett. Org. Chem."},{"key":"10.1016\/j.ejmech.2018.12.038_bib61","unstructured":"Attempted synthesis of 6h with condensing agents different than arenesulfonyl chlorides, failed. Carrying out the reaction with TPSCl in different solvents, in combination with other nucleophilic catalysts, and by changing purification conditions, did not produce the expected results. Since in the HRMS spectrum only a molecular peak from 6h was present, this lend support for the formation of a complex rather than covalent attachment of TPSOH to this compound. On the biology part, since an anti-HIV activity of TPSOH is not likely, we included the obtained compound 6h x 0.5 TPSOH in such a form into our biological studies."},{"key":"10.1016\/j.ejmech.2018.12.038_bib62","unstructured":"The main product of the reaction (ca 50%) gave a pair of signals at 1.74 and 1.85 ppm in the 31P NMR spectrum, suggesting formation of P-diastereomers of an unidentified compound that could not be isolated due to its instability."},{"key":"10.1016\/j.ejmech.2018.12.038_bib63","unstructured":"One should note that 4-hydroxypyridine can exist in two tautomeric forms and the estimated pKa value of 7.7 was based on the assumed ratio of 4-hydroxypyridone : 4-hydroxypyridine being ca 2200. The authors themselves suggested to treat this value as 'approximate' (see ref. [58] by Bradamante and Pagini)."},{"key":"10.1016\/j.ejmech.2018.12.038_bib64","doi-asserted-by":"crossref","first-page":"2385","DOI":"10.1016\/S0040-4039(00)93156-3","article-title":"Syntheses and configurational assignments of the diastereomers of the 4-nitrophenyl esters of thymidine 3\u2019-N-phenyl phosphoramidate) and thymidine 5\u2019-(N-phenyl phosphoramidate)","volume":"21","author":"Gerlt","year":"1980","journal-title":"Tetrahedron Lett."},{"key":"10.1016\/j.ejmech.2018.12.038_bib65","doi-asserted-by":"crossref","first-page":"4569","DOI":"10.1021\/jm9603680","article-title":"Synthesis and biological activity of aromatic amino acid phosphoramidates of 5-Fluoro-2'-deoxyuridine and 1-b-Arabinofuranosylcytosine: evidence of phosphoramidase activity","volume":"39","author":"Abraham","year":"1996","journal-title":"J.\u00a0Med. Chem."},{"key":"10.1016\/j.ejmech.2018.12.038_bib66","doi-asserted-by":"crossref","first-page":"913","DOI":"10.1080\/15257779908041599","article-title":"Antiviral nucleoside drug delivery via amino acid phosphoramidates","volume":"18","author":"Wagner","year":"1999","journal-title":"Nucleos Nucleot."},{"key":"10.1016\/j.ejmech.2018.12.038_bib67","doi-asserted-by":"crossref","first-page":"888","DOI":"10.1039\/b9nj00660e","article-title":"Recognition of different nucleotidyl-derivatives as substrates of reactions catalyzed by various HIT-proteins","volume":"34","author":"Guranowski","year":"2010","journal-title":"New J. Chem."},{"key":"10.1016\/j.ejmech.2018.12.038_bib68","doi-asserted-by":"crossref","first-page":"157","DOI":"10.1016\/S0026-895X(25)09957-2","article-title":"Potent DNA chain termination activity and selective inhibition of human immunodeficiency virus reverse transcriptase by 2',3'-dideoxyuridine-5'-triphosphate","volume":"37","author":"Hao","year":"1990","journal-title":"Mol. 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New anti-HIV pronucleotide phosphoramidate diesters containing amino- and hydroxypyridine auxiliaries","name":"articletitle","label":"Article Title"},{"value":"European Journal of Medicinal Chemistry","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.ejmech.2018.12.038","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"\u00a9 2018 Elsevier Masson SAS. All rights reserved.","name":"copyright","label":"Copyright"}]}}