{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,3]],"date-time":"2026-10-03T07:38:01Z","timestamp":1791013081590,"version":"4.1.0"},"reference-count":31,"publisher":"Elsevier BV","content-domain":{"domain":["elsevier.com","sciencedirect.com"],"crossmark-restriction":true},"short-container-title":["European Journal of Medicinal Chemistry"],"published-print":{"date-parts":[[2013,9]]},"DOI":"10.1016\/j.ejmech.2013.06.053","type":"journal-article","created":{"date-parts":[[2013,7,4]],"date-time":"2013-07-04T17:25:14Z","timestamp":1372958714000},"page":"398-408","update-policy":"https:\/\/doi.org\/10.1016\/elsevier_cm_policy","source":"Crossref","is-referenced-by-count":31,"special_numbering":"C","title":["Synthesis and broad spectrum antiviral evaluation of bis(POM) prodrugs of novel acyclic nucleosides"],"prefix":"10.1016","volume":"67","author":[{"given":"Manabu","family":"Hamada","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Vincent","family":"Roy","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tamara R.","family":"McBrayer","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tony","family":"Whitaker","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Cesar","family":"Urbina-Blanco","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Steven P.","family":"Nolan","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jan","family":"Balzarini","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Robert","family":"Snoeck","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Graciela","family":"Andrei","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Raymond F.","family":"Schinazi","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Luigi A.","family":"Agrofoglio","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"78","reference":[{"key":"10.1016\/j.ejmech.2013.06.053_bib1","series-title":"Herpesviridae \u2013 a Look into This Unique Family of Viruses","first-page":"245","article-title":"Nucleoside and nucleotide analogues for the treatment of herpesvirus infections: current stage and new prospects in the field of acyclic nucleoside phosphonates","author":"Kre\u010dmerov\u00e1","year":"2012"},{"key":"10.1016\/j.ejmech.2013.06.053_bib2","series-title":"Current Protocols in Nucleic Acid Chemistry","article-title":"Synthesis of acyclic nucleoside phosphonates","author":"Hol\u00fd","year":"2005"},{"key":"10.1016\/j.ejmech.2013.06.053_bib3","doi-asserted-by":"crossref","first-page":"928","DOI":"10.1038\/nrd1877","article-title":"Acyclic nucleoside phosphonates: a key class of antiviral drugs","volume":"4","author":"De Clercq","year":"2005","journal-title":"Nat. Rev. Drug Discov."},{"key":"10.1016\/j.ejmech.2013.06.053_bib4","doi-asserted-by":"crossref","first-page":"480","DOI":"10.1135\/cccc2011065","article-title":"Acyclic nucleoside phosphonates: an unfinished story","volume":"76","author":"De Clercq","year":"2011","journal-title":"Collect. Czech. Chem. Commun."},{"key":"10.1016\/j.ejmech.2013.06.053_bib5","doi-asserted-by":"crossref","first-page":"115","DOI":"10.1177\/095632029600700301","article-title":"Cidofovir, a new agent with potent anti-herpesvirus activity","volume":"7","author":"Hitchcok","year":"1996","journal-title":"Antivir. Chem. Chemother."},{"key":"10.1016\/j.ejmech.2013.06.053_bib6","doi-asserted-by":"crossref","first-page":"464","DOI":"10.1038\/323464a0","article-title":"A\u00a0novel selective broad-spectrum anti-DNA virus agent","volume":"323","author":"De Clercq","year":"1986","journal-title":"Nature"},{"key":"10.1016\/j.ejmech.2013.06.053_bib7","doi-asserted-by":"crossref","first-page":"332e338","DOI":"10.1128\/AAC.37.2.332","article-title":"Differential antiherpesvirus and antiretrovirus effects of the (S) and (R) enantiomers of acyclic nucleoside phosphonates: potent and selective in\u00a0vitro and in\u00a0vivo antiretrovirus activities of (R)-9-(2-Phosphonylme thoxypropyl)-2,6-diaminopurine","volume":"37","author":"Balzarini","year":"1993","journal-title":"Antimicrob. Agents Chemother."},{"key":"10.1016\/j.ejmech.2013.06.053_bib8","doi-asserted-by":"crossref","first-page":"222","DOI":"10.1021\/jm1011462","article-title":"Novel antiviral C5-substituted pyrimidine acyclic nucleoside phosphonates selected as human thymidylate kinase substrates","volume":"54","author":"Topalis","year":"2011","journal-title":"J.\u00a0Med. Chem."},{"key":"10.1016\/j.ejmech.2013.06.053_bib9","doi-asserted-by":"crossref","first-page":"7324","DOI":"10.1002\/ejoc.201101111","article-title":"The shortest strategy for generating phosphonate prodrugs by olefin cross metathesis \u2013 application to acyclonucleoside phosphonates","volume":"36","author":"Prad\u00e8re","year":"2011","journal-title":"Eur. J. Org. Chem."},{"key":"10.1016\/j.ejmech.2013.06.053_bib10","doi-asserted-by":"crossref","first-page":"5319","DOI":"10.1016\/j.tet.2011.05.017","article-title":"Expeditious convergent procedure for the preparation of bis(POC) prodrugs of (E)-4-phosphono-but-2-en-1-yl nucleoside","volume":"67","author":"Montagu","year":"2001","journal-title":"Tetrahedron"},{"key":"10.1016\/j.ejmech.2013.06.053_bib11","first-page":"2127","article-title":"Microwave assisted silylation-amination of uracil acyclonucleosides to 4-alkylamino-2(1H)-pyrimidone analogues","volume":"13","author":"Roy","year":"2008","journal-title":"Synthesis"},{"key":"10.1016\/j.ejmech.2013.06.053_bib12","doi-asserted-by":"crossref","first-page":"105","DOI":"10.1111\/j.1349-7006.2004.tb03189.x","article-title":"Antitumor activity of sugar-modified nucleosides","volume":"95","author":"Matsuda","year":"2004","journal-title":"Cancer Sci."},{"key":"10.1016\/j.ejmech.2013.06.053_bib13","doi-asserted-by":"crossref","first-page":"185","DOI":"10.2174\/138527206775192942","article-title":"Ruthenium-catalyzed ring-closing metathesis: recent advances, limitations and opportunities","volume":"10","author":"Conrad","year":"2006","journal-title":"Curr. Org. Chem."},{"key":"10.1016\/j.ejmech.2013.06.053_bib14","doi-asserted-by":"crossref","first-page":"9183","DOI":"10.1021\/jo061694i","article-title":"Efficient N-arylation and N-alkenylation of the five DNA\/RNA nucleobases","volume":"71","author":"Jacobsen","year":"2006","journal-title":"J.\u00a0Org. Chem."},{"issue":"34","key":"10.1016\/j.ejmech.2013.06.053_bib15","doi-asserted-by":"crossref","first-page":"5786","DOI":"10.1002\/ejoc.200800891","article-title":"A\u00a0practical and efficient approach to PNA monomers compatible with Fmoc-mediated solid-phase synthesis protocols","author":"Porcheddu","year":"2008","journal-title":"Eur. J. Org. Chem."},{"key":"10.1016\/j.ejmech.2013.06.053_bib16","doi-asserted-by":"crossref","first-page":"2035","DOI":"10.1016\/0040-4039(96)00211-0","article-title":"Ceric ammonium nitrate in the deprotection of tert-butoxycarbonyl group","volume":"37","author":"Hwu","year":"1996","journal-title":"Tetrahedron Lett."},{"key":"10.1016\/j.ejmech.2013.06.053_bib17","doi-asserted-by":"crossref","first-page":"981","DOI":"10.1128\/AAC.49.3.981-986.2005","article-title":"Mechanism of action of T-705 against influenza virus","volume":"49","author":"Furuta","year":"2005","journal-title":"Antimicrob. Agents Chemother."},{"key":"10.1016\/j.ejmech.2013.06.053_bib18","doi-asserted-by":"crossref","first-page":"845","DOI":"10.1128\/AAC.01051-06","article-title":"Efficacy of orally administered T-705 on lethal avian influenza A (H5N1) virus infections in mice","volume":"51","author":"Sidwell","year":"2007","journal-title":"Antimicrob. Agents Chemother."},{"key":"10.1016\/j.ejmech.2013.06.053_bib19","doi-asserted-by":"crossref","first-page":"1150","DOI":"10.1021\/jm00281a014","article-title":"Design, synthesis, and broad spectrum antiviral activity of 1-beta-D-ribofuranosyl-1,2,4-triazole-3-carboxamide and related nucleosides","volume":"15","author":"Witkowski","year":"1972","journal-title":"J.\u00a0Med. Chem."},{"key":"10.1016\/j.ejmech.2013.06.053_bib20","doi-asserted-by":"crossref","first-page":"487","DOI":"10.1080\/07328319108046503","article-title":"Synthesis and biological evaluation of carbocyclic analogues of ribavirin","volume":"10","author":"Noble","year":"1991","journal-title":"Nucleosides Nucleotides"},{"key":"10.1016\/j.ejmech.2013.06.053_bib21","doi-asserted-by":"crossref","first-page":"3633","DOI":"10.1016\/S0968-0896(03)00349-3","article-title":"Synthesis of 1,2,3-triazolo-carbanucleoside analogues of ribavirin targeting an HCV in replicon","volume":"11","author":"Saito","year":"2003","journal-title":"Bioorg. Med. Chem."},{"key":"10.1016\/j.ejmech.2013.06.053_bib22","doi-asserted-by":"crossref","first-page":"4207","DOI":"10.1021\/cr9001462","article-title":"Cu(I)-catalyzed Huisgen azide\u2013alkyne 1,3-dipolar cycloaddition reaction in nucleoside, nucleotide, and oligonucleotide chemistry","volume":"109","author":"Amblard","year":"2009","journal-title":"Chem. Rev."},{"key":"10.1016\/j.ejmech.2013.06.053_bib23","doi-asserted-by":"crossref","first-page":"177","DOI":"10.4155\/fmc.09.156","article-title":"Microwave-assisted syntheses of nucleosides and their precursors","volume":"2","author":"Roy","year":"2010","journal-title":"Future Med. Chem."},{"key":"10.1016\/j.ejmech.2013.06.053_bib24","doi-asserted-by":"crossref","first-page":"9044","DOI":"10.1016\/j.tet.2008.07.007","article-title":"Preparation of ribavirin analogues by copper- and ruthenium-catalyzed azide-alkyne 1,3-dipolar cycloaddition","volume":"64","author":"Pradere","year":"2008","journal-title":"Tetrahedron"},{"key":"10.1016\/j.ejmech.2013.06.053_bib25","doi-asserted-by":"crossref","first-page":"4185","DOI":"10.1021\/jm00050a015","article-title":"1,2,3-Triazole-[2,5-bis-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]-3\u2032-spiro-5\u2032-(4\u2032-amino-1\u2032,2\u2032-oxathiole 2\u2032,2\u2032-dioxide) (TSAO) analogs: synthesis and anti-HIV-1 activity","volume":"37","author":"Alvarez","year":"1994","journal-title":"J.\u00a0Med. Chem."},{"key":"10.1016\/j.ejmech.2013.06.053_bib26","first-page":"223","article-title":"A\u00a0novel approach to 1-monosubstituted 1,2,3-triazoles by a click cycloaddition\/decarboxylation process","author":"Xu","year":"2011","journal-title":"Synthesis"},{"key":"10.1016\/j.ejmech.2013.06.053_bib27","doi-asserted-by":"crossref","first-page":"5454","DOI":"10.1002\/chem.200903484","article-title":"Boronic acid catalysis for mild and selective [3+2] dipolar cycloadditions to unsaturated carboxylic acids","volume":"16","author":"Zheng","year":"2010","journal-title":"Chem. Eur. J."},{"key":"10.1016\/j.ejmech.2013.06.053_bib28","doi-asserted-by":"crossref","first-page":"244","DOI":"10.1128\/AAC.47.1.244-254.2003","article-title":"Ribonucleoside analogue that blocks replication of bovine viral diarrhea and hepatitis C viruses in culture","volume":"47","author":"Stuyver","year":"2003","journal-title":"Antimicrob. Agents Chemother."},{"key":"10.1016\/j.ejmech.2013.06.053_bib29","doi-asserted-by":"crossref","first-page":"1061","DOI":"10.1128\/AAC.34.6.1061","article-title":"Activities of 3\u2032-azido-3\u2032-deoxythymidine nucleotide dimers in primary lymphocytes infected with human immunodeficiency virus type 1","volume":"34","author":"Schinazi","year":"1990","journal-title":"Antimicrob. Agents Chemother."},{"key":"10.1016\/j.ejmech.2013.06.053_bib30","doi-asserted-by":"crossref","first-page":"3854","DOI":"10.1128\/AAC.46.12.3854-3860.2002","article-title":"Antiviral activities and cellular toxicities of modified 2\u2032,3\u2032-dideoxy-2\u2032,3\u2032-didehydrocytidine analogues","volume":"46","author":"Stuyver","year":"2002","journal-title":"Antimicrob. Agents Chemother."},{"key":"10.1016\/j.ejmech.2013.06.053_bib31","first-page":"493","article-title":"A\u00a0simple method of estimating fifty percent endpoints","volume":"27","author":"Reed","year":"1938","journal-title":"Am. J. Hyg."}],"container-title":["European Journal of Medicinal Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0223523413004212?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0223523413004212?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2018,10,14]],"date-time":"2018-10-14T20:56:24Z","timestamp":1539550584000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0223523413004212"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2013,9]]},"references-count":31,"alternative-id":["S0223523413004212"],"URL":"https:\/\/doi.org\/10.1016\/j.ejmech.2013.06.053","relation":{},"ISSN":["0223-5234"],"issn-type":[{"value":"0223-5234","type":"print"}],"subject":[],"published":{"date-parts":[[2013,9]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"Synthesis and broad spectrum antiviral evaluation of bis(POM) prodrugs of novel acyclic nucleosides","name":"articletitle","label":"Article Title"},{"value":"European Journal of Medicinal Chemistry","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.ejmech.2013.06.053","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"Copyright \u00a9 2013 Elsevier Masson SAS. Published by Elsevier Masson SAS All rights reserved.","name":"copyright","label":"Copyright"}]}}