{"@context":{"@vocab":"https://cir.nii.ac.jp/schema/1.0/","rdfs":"http://www.w3.org/2000/01/rdf-schema#","dc":"http://purl.org/dc/elements/1.1/","dcterms":"http://purl.org/dc/terms/","foaf":"http://xmlns.com/foaf/0.1/","prism":"http://prismstandard.org/namespaces/basic/2.0/","cinii":"http://ci.nii.ac.jp/ns/1.0/","datacite":"https://schema.datacite.org/meta/kernel-4/","ndl":"http://ndl.go.jp/dcndl/terms/","jpcoar":"https://github.com/JPCOAR/schema/blob/master/2.0/"},"@id":"https://cir.nii.ac.jp/crid/1390282679142187904.json","@type":"Article","productIdentifier":[{"identifier":{"@type":"DOI","@value":"10.1248/cpb.36.4153"}},{"identifier":{"@type":"URI","@value":"http://www.jstage.jst.go.jp/article/cpb1958/36/10/36_10_4153/_pdf"}},{"identifier":{"@type":"NAID","@value":"130003944151"}}],"dc:title":[{"@language":"en","@value":"8-Aza-7-deaza-2',3'-dideoxyadenosine: Synthesis and conversion into allopurinol 2',3'-dideoxyribofuranoside."}],"dc:language":"en","description":[{"type":"abstract","notation":[{"@language":"en","@value":"4-Amino-1-(2, 3-dideoxy-β-D-<I>glycero</I>-pentofuranosyl)-1<I>H</I>-pyrazolo [3, 4-d] pyrimidine (<B>5</B>) was synthesized from 8-aza-7-deaza-2'-deoxyadenosine (<B>1</B>). Benzoylation of the 4-amino group of <B>1</B> followed by 4, 4'-dimethoxytritylation of the 5'-hydroxyl function gave <B>2b</B>. Barton deoxygenation of the phenoxythiocarbonyl compound <B>3</B> afforded <B>4a</B> and yielded <B>5</B> after removal of the protecting groups. The <I>N</I>-glycosylic bond stability of <B>5</B> to acid was higher than that of 2', 3'-dideoxyadenosine (ddA). Compound <B>5</B> showed no appreciable activity against human immunodeficiency virus. It was converted into allopurinol 2', 3'-dideoxyribofuranoside (<B>6</B>) by adenosine deaminase but at a lower rate than the conversion of ddA into ddl."}],"abstractLicenseFlag":"disallow"}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1410282679142187904","@type":"Researcher","personIdentifier":[{"@type":"NRID","@value":"9000254698117"}],"foaf:name":[{"@language":"en","@value":"SEELA FRANK"}],"jpcoar:affiliationName":[{"@language":"en","@value":"Laboratorium für Organische und Bioorganische Chemie, Fachbereich Biologie/Chemie, Universität Osnabrück"}]},{"@id":"https://cir.nii.ac.jp/crid/1410282679142187905","@type":"Researcher","personIdentifier":[{"@type":"NRID","@value":"9000254698118"}],"foaf:name":[{"@language":"en","@value":"KAISER KLAUS"}],"jpcoar:affiliationName":[{"@language":"en","@value":"Laboratorium für Organische und Bioorganische Chemie, Fachbereich Biologie/Chemie, Universität Osnabrück"}]}],"publication":{"publicationIdentifier":[{"@type":"PISSN","@value":"00092363"},{"@type":"EISSN","@value":"13475223"}],"prism:publicationName":[{"@language":"ja","@value":"ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ"},{"@language":"en","@value":"Chemical and Pharmaceutical Bulletin"},{"@language":"en","@value":"Chem. Pharm. Bull."},{"@language":"en","@value":"CHEMICAL & PHARMACEUTICAL BULLETIN"},{"@language":"ja","@value":"Ｃｈｅｍ．　Ｐｈａｒｍ．　Ｂｕｌｌ．"}],"dc:publisher":[{"@language":"en","@value":"The Pharmaceutical Society of Japan"},{"@language":"ja","@value":"公益社団法人 日本薬学会"}],"prism:publicationDate":"1988","prism:volume":"36","prism:number":"10","prism:startingPage":"4153","prism:endingPage":"4156"},"reviewed":"false","url":[{"@id":"http://www.jstage.jst.go.jp/article/cpb1958/36/10/36_10_4153/_pdf"}],"availableAt":"1988","foaf:topic":[{"@id":"https://cir.nii.ac.jp/all?q=8-aza-7-deaza-2',%203'-dideoxyadenosine","dc:title":"8-aza-7-deaza-2', 3'-dideoxyadenosine"},{"@id":"https://cir.nii.ac.jp/all?q=allopurinol%202',%203'-dideoxyribofuranoside","dc:title":"allopurinol 2', 3'-dideoxyribofuranoside"},{"@id":"https://cir.nii.ac.jp/all?q=pyrazolo%20%5B3,%204-%3CI%3Ed%3C/I%3E%5D%20pyrimidine","dc:title":"pyrazolo [3, 4-<I>d</I>] pyrimidine"},{"@id":"https://cir.nii.ac.jp/all?q=Barton%20deoxygenation","dc:title":"Barton deoxygenation"},{"@id":"https://cir.nii.ac.jp/all?q=%3CI%3EN%3C/I%3E-glycosylic%20bond%20stability","dc:title":"<I>N</I>-glycosylic bond stability"},{"@id":"https://cir.nii.ac.jp/all?q=anti-HIV%20activity","dc:title":"anti-HIV activity"},{"@id":"https://cir.nii.ac.jp/all?q=adenosine%20deaminase","dc:title":"adenosine deaminase"}],"dataSourceIdentifier":[{"@type":"JALC","@value":"oai:japanlinkcenter.org:0022288569"},{"@type":"CROSSREF","@value":"10.1248/cpb.36.4153"},{"@type":"CIA","@value":"130003944151"}]}