Synthesis and Biological Activity of C-Acyclic Nucleosides of Imidazo [1,5-a]-1,3,5-Triazines |
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| Authors: | Bozenna Golankiewicz Joanna Zeidler Erik De Clercq |
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| Institution: | 1. Institute of Bioorganic Chemistry, Polish Academy of Sciences , Noskowskiego 12/14, 61-704, Poznan, Poland;2. Rega Institute for Medical Research, Katholieke Universiteit Leuven , B-3000, Leuven, Belgium |
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| Abstract: | Abstract C-acyclic nucleoside analogues of inosine and guanosine 8-(RS)-2,3-dihydroxypropyl] imidazo 1,5-a]-1,3,5-triazin-4 (3H)-ones 6a, c, d were synthesized. The route involved the cyclization-rearrangement of 5-acylamino-5-allyl-6-amino-4,5-dihydropyrimidin-4-ones 4a-c to 8-allylimidazo 1,5-a]-1,3,5-triazin-4 (3H) ones 5a-c. 5a was transformed selectively into 5d by reductive desulfurization with highly deactivated Raney nickel. The poorly soluble compounds 5b and 5c were converted to N-2-acetylated 5f and 5g. Osmium tetroxide hydroxylation of 5d, f, g gave 6a, c, d. None of the newly synthesized C-acyclic nucleoside derivatives showed an appreciable antiviral or antitumor cell activity. |
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