Synthesis of novel 2',3'-dideoxy-6-azacytidine derivatives – potential retroviral reproduction inhibitors
DOI:
https://doi.org/10.7124/bc.0005E1Abstract
This paper deals with the synthesis of the novel 2',3'-dihalo-2',3'-dideoxy- and 2',3'-didehydro-2',3'-dideoxy-analogues of 6-azacytidine as potential antiviral substances. The compounds were prepared by means of the appropriate reagents – triphenylphosphonium halogen salts. The first step of the 6-azacytidine conversion results in 2,3-epoxynucleosides as against deoxygenation of uridine and thymidine, when O2, 2'-cyclonucleosides are generated.References
Kraevski? AA. Molecular bases in the search for drugs for treating AIDS. Achievements and possible prospects. Mol Biol (Mosk). 1999;33(3):343-52.
De Clercq E. Antiviral Activity Spectrum of Nucleoside and Nucleotide Analogues. Nucleosides Nucleotides. 1991;10(1-3):167-80.
De Clercq E. HIV inhibitors targeted at the reverse transcriptase. AIDS Res Hum Retroviruses. 1992;8(2):119-34.
Mizuno Y, Mizuo Y, Itoh T, Nomura A. Azanucleosides and Deazanucleosides of Biological Interest. Heterocycles. 1982;17(1):615-44.
Shalamay AS. Iodination reaction of carbohydrate of pyrimidine nucleosides as perspective method preparation of antiretroviral drugs. Biopolym Cell. 1998; 14(4):371-80.
Moffatt JG. Chemical transformation of the sugar moiety of nucleosides. New York, 1979. 127 p.
Kostina VG, Shalamay AS, Vsenko LS. Synthesis of 2', 3'-didehydro-2', 3'-dideoxyuridine with following addition of triphenylphosphonium iodides. Biopolym Cell. 1996; 12(4):100-4.
Kostina VG, Shalamoy AS, Vsenko LS, Gladkaya VA. Study of iodination mechanism of 5'-O-prolecled pyrimidine Hucleosides in Arbuzov reaction conditions. Biopolym Cell. 1998; 14(3):246-51.
Gordon A, Ford R. Sputnik Khimika M.: Mir, 1976. 541 p.
Beranek J, Sorm F. Nucleic acid components and their analogues. CIX. Synthesis of 1-?-D-arabinofuranosyl-6-azaisocytosine. Collect Czechoslov Chem Commun. 1968;33(3):913-23.
Lin T-S, Yang J-H, Gao Y-S. Synthesis of 2?,3?-Unsaturated and 2?, 3?-Dideoxy Analogs of 6-Azapyrimidine Nucleosides as Potential Anti-Hiv Agents. Nucleosides Nucleotides. 1990;9(1):97–108.
Robins MJ, Fouron Y, Mengel R. Nucleic acid related compounds. 11. Adenosine 2',3'-ribo-epoxide. Synthesis, intramolecular degradation, and transformation into 3'-substituted xylofuranosyl nucleosides and the lyxo-epoxide. J Org Chem. 1974;39(11):1564-70.
Mitchell WL, Ravenscroft P, Hill ML, Knutsen LJ, Judkins BD, Newton RF, Scopes DI. Synthesis and antiviral properties of 5-(2-substituted vinyl)-6-aza-2'-deoxyuridines. J Med Chem. 1986;29(5):809-16.
Wieczorkowski J, Sorm F, Beranek J. Nucleic acid components and their analogues. CX. Synthesis of 1-(2',3'-epoxy-?-D-lyxofuranosyl)-6-azaisocytosine. Collect Czechoslov Chem Commun. 1968; 33(3):924-930.
