Synthesis and antiviral activities of N-9-oxypurine 1,3-dioxolane and 1,3-oxathiolane nucleosides.

Two series of 1,3-dioxolanes and 1,3-oxathiolane nucleosides containing N-9-oxypurine were synthesized as potential antiviral agents. These compounds were prepared by reacting the sugar moieties with iodo- or bromotrimethylsilane, followed by treatment with a mixture of sodium hydride and the desired N-hydroxy purine base. The preparation of these N-hydroxybases was also described. No significant antiviral activity was observed against HIV, HBV, HSV-1, HSV-2, or HCMV.

[1]  A. Parkin,et al.  Synthesis of 5-Amino-4-aminocarbonyl-1-hydroxyimidazole and its Conversion to Novel Acyclic Analogues of AICA Riboside , 1990 .

[2]  E. Grochowski,et al.  The Synthesis of "C-O-N" Analogues of Nucleosides via the Mitsunobu Reaction , 1988 .

[3]  M. Kukhanova,et al.  Beta-L-(-)-dioxolane Cytidine (β-L-(-)-OddC) as a Potent Compound for the Treatment of Cancer , 1997 .

[4]  H. Mitsuya,et al.  Inhibition of the in vitro infectivity and cytopathic effect of human T-lymphotrophic virus type III/lymphadenopathy-associated virus (HTLV-III/LAV) by 2',3'-dideoxynucleosides. , 1986, Proceedings of the National Academy of Sciences of the United States of America.

[5]  D W Barry,et al.  3'-Azido-3'-deoxythymidine (BW A509U): an antiviral agent that inhibits the infectivity and cytopathic effect of human T-lymphotropic virus type III/lymphadenopathy-associated virus in vitro. , 1985, Proceedings of the National Academy of Sciences of the United States of America.

[6]  Erik De Clercq,et al.  Toward improved anti-HIV chemotherapy: therapeutic strategies for intervention with HIV infections. , 1995 .

[7]  P. Wyatt,et al.  Synthesis of 9-hydroxypurines: Intermediates to novel antiviral acyclonucleosides , 1990 .

[8]  A. A. Watson Purine N-oxides. LVII. 9-Hydroxyhypoxanthine, xanthine, and guanine. , 1974, The Journal of organic chemistry.

[9]  L. Brasili,et al.  A novel class of 1,3-oxathiolane nucleoside analogues having potent anti-HIV activity , 1993 .

[10]  L. Brasili,et al.  Synthesis and anti-HIV activity of 1,3-dithiolane nucleosides , 1999 .