[Ribonucleoside and 2'-deoxyribonucleoside 5'-phosphonates: synthesis and antiviral activity].
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.
Shirokova
E A
EA
Ias'ko
M V
MV
Shipitsyn
A V
AV
Kraevskiĭ
A A
AA
Ostrander
M
M
O'Hara
B
B
Baron
P
P
Maclow
K
K
Polsky
B
B
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
D000998:Antiviral Agents; D003853:Deoxyribonucleosides; D009943:Organophosphorus Compounds; D012263:Ribonucleosides
5'-Fosfonaty ribonukleozidov i 2'-dezoksiribonukleozidov: sintez i antivirusnaia aktivnost'.