5'-phosphorates of ribonucleosides and 2,-deoxyribonucleosides: Synthesis and antiviral activity Journal Article
| Authors: | Jasko, M.; Shipitsin, A.; Slirokova, E.; Krayevsky, A.; Polsky, B.; Baron, P.; MacLow, C.; Ostrander, M.; O'Hara, B. |
| Article Title: | 5'-phosphorates of ribonucleosides and 2,-deoxyribonucleosides: Synthesis and antiviral activity |
| Abstract: | 5'-Phosphonates of natural 2'-deoxynucleosides and ribonucleosides were synthesized by condensation of 3'-O-acylated 2'-deoxynucleosides or 2',3'-substituted (2',3'-0-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'-ethoxycarbonylphosphonates were converted into corresponding nucleoside 5'-aminocarbonylphosphonates by action of ammonia in methanol or aqueous ammonia. 5'-Hydrogenphosphonothioates of thymidine and 3'-deoxythymidine were obtained by reaction of phosphinic acid in the presence of pivaloyl chloride with 3'-O-acetylthymidine or 3'-deoxythymidine, respectively, followed by addition of powedered sulfur. 5'-O-methylenephosplionates of thymidine and 2'-deoxyadenosine were prepared by intramolecular reaction of corresponding 3'-O-iodomethylphosphonates under basic conditions. All compounds were tested for inhibition of several viruses, including HSV-2 and CMV, but showed no activity. A few compounds insignificantly inhibited HIV-1 reproduction. Thymidine 5'-hydrogenphosphonate neutralized anti-HIV action of 3'-azido-3'-deoxythymidine (AZT) and it indirectly showed that even some nucleoside 5'-phosphonates could be partly hydrolyzed in cell culture to corresponding nucleosides. © 1993, Taylor & Francis Group, LLC. All rights reserved. |
| Keywords: | dna replication; dna synthesis; cell culture; rna synthesis; virus replication; nuclear magnetic resonance; antiviral activity; ribonucleoside; article; deoxyribonucleoside; cmv - human cytomegalovirus; flua influenca a virus; hiv - human immunodeficiency virus; hsv - human herpes symplex virus; vv -vaccinia virus |
| Journal Title: | Nucleosides & Nucleotides |
| Volume: | 12 |
| Issue: | 8 |
| ISSN: | 0732-8311 |
| Publisher: | Taylor & Francis Inc. |
| Date Published: | 1993-11-01 |
| Start Page: | 879 |
| End Page: | 893 |
| Language: | English |
| DOI: | 10.1080/07328319308018558 |
| PROVIDER: | scopus |
| DOI/URL: | |
| Notes: | Article -- Export Date: 1 March 2019 -- Source: Scopus |
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