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Herein, we report the synthesis and antiviral activity of a series of phosphoramidate ProTides designed to bypass the thymidine kinase (TK) dependence of the parent nucleoside analogues. Phosphoramidate derivatives of (<jats:italic>E<\/jats:italic>)\u20105\u2010(2\u2010bromovinyl)\u20102\u2032\u2010deoxyuridine (BVDU) that contain <jats:sc>L<\/jats:sc>\u2010alanine or pivaloyloxymethyl iminodiacetate (IDA\u2010POM) exhibit anti\u2010HSV\u20101 and anti\u2010VZV activity in cell cultures, but they largely lost antiviral potency against TK\u2010deficient virus strains. Among deazapurine nucleosides and their phosphoramidate derivatives, the 7\u2010deazaadenine containing nucleosides and their phosphoramidate triester derivatives showed weak antiviral activity against VZV. Apparently, intracellular nucleotide delivery with these phosphoramidates is partly successful. However, none of the compound prodrugs showed superior activity to their parent drugs.<\/jats:p>","DOI":"10.1002\/cmdc.201300035","type":"journal-article","created":{"date-parts":[[2013,4,18]],"date-time":"2013-04-18T16:07:54Z","timestamp":1366301274000},"page":"985-993","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":13,"title":["Synthesis and Anti\u2010herpetic Activity of Phosphoramidate ProTides"],"prefix":"10.1002","volume":"8","author":[{"given":"Munmun","family":"Maiti","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Leentje","family":"Persoons","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Graciela","family":"Andrei","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Robert","family":"Snoeck","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jan","family":"Balzarini","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Piet","family":"Herdewijn","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2013,4,18]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0065-3527(09)73001-5"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ijantimicag.2012.04.005"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/med.20011"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.78.5.2698"},{"key":"e_1_2_6_6_2","doi-asserted-by":"crossref","first-page":"432","DOI":"10.1016\/S0026-895X(25)14611-7","volume":"21","author":"Fyfe J. 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