title: [Ribonucleoside and 2'-deoxyribonucleoside 5'-phosphonates: synthesis and antiviral activity].
abstract: Groups of 5'-phosphonates of natural 2'-deoxynucleosides and ribonucleosides were synthesized by condensation of 3'-acetylated 2'-deoxynucleosides or 2',3'-substituted (2',3'-O-isopropylidene, 2',3'-O-methoxymethylene, or 2',3'-O-ethoxymethylene) ribonucleosides. As condensing agents, either N,N'-dicyclohexylcarbodiimide or 2,4,6-triisopropylbenzenesulphonyl chloride were used. Nucleoside 5'-ethoxycarbonyl-phosphonates were converted into corresponding nucleoside 5'-aminocarbonylphosphonates by the action of ammonia in methanol. All compounds were tested for inhibition of several viruses, including human herpes simplex virus type 2 and cytomegalovirus, but showed no activity. A few compounds insignificantly inhibited human immunodeficiency virus type 1 reproduction. Thymidine 5'-hydrogenphosphonate neutralized the anti HIV action of 3'-azido-3'-deoxythymidine, thus indirectly showing that it could be partly hydrolyzed in cell culture to corresponding thymidine.
authors.forename: E A
authors.initials: EA
authors.lastname: Shirokova
authors.forename: M V
authors.initials: MV
authors.lastname: Ias'ko
authors.forename: A V
authors.initials: AV
authors.lastname: Shipitsyn
authors.forename: A A
authors.initials: AA
authors.lastname: Kraevskiĭ
authors.forename: M
authors.initials: M
authors.lastname: Ostrander
authors.forename: B
authors.initials: B
authors.lastname: O'Hara
authors.forename: P
authors.initials: P
authors.lastname: Baron
authors.forename: K
authors.initials: K
authors.lastname: Maclow
authors.forename: B
authors.initials: B
authors.lastname: Polsky
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D002478:Cells, Cultured; D003587:Cytomegalovirus / Q000187:drug effects / Q000502:physiology; D003853:Deoxyribonucleosides / Q000737:chemistry* / Q000494:pharmacology; D015497:HIV-1 / Q000187:drug effects / Q000502:physiology; D009943:Organophosphorus Compounds / Q000737:chemistry*; D012263:Ribonucleosides / Q000737:chemistry* / Q000494:pharmacology; D018139:Simplexvirus / Q000187:drug effects / Q000502:physiology; D014779:Virus Replication / Q000187:drug effects
chemical_list: D000998:Antiviral Agents; D003853:Deoxyribonucleosides; D009943:Organophosphorus Compounds; D012263:Ribonucleosides
vernacular_title: 5'-Fosfonaty ribonukleozidov i 2'-dezoksiribonukleozidov: sintez i antivirusnaia aktivnost'.