Synthesis of (S)-1-(2',3'-dihydroxypropyl)-2-alkylthiouracils as new antiviral agents.
2-Alkylthiouracils 1a-f have been prepared. Nucleoside coupling of 2 with sodium salt of 1a-f gave the corresponding dioxolane derivatives 3a-f which were treated with 80% acetic acid at reflux temperature to give (S)-1-(2',3'-dihydroxypropyl)-2-alkylthiouracil derivatives 4a-f. Treatment of 4d with 1 mol tosyl chloride gives the corresponding monotosylate 5. On the other hand, with 2 mol it gives the ditosylate 6. Treatment of 5 and/or 6 with sodium azide/dimethylformamide give 7 and 8 which could be reduced to the corresponding amino derivatives 9 and 10 by using triphenylphosphine/pyridine.
Rahman
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Chemistry Department, Faculty of Science, Menoufia University, Shebin El-Koam, Egypt.
Aal
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MT
D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D006515:Hepatitis B virus / Q000187:drug effects / Q000502:physiology; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D013889:Thiouracil / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology; D014779:Virus Replication / Q000187:drug effects
D019380:Anti-HIV Agents; D013889:Thiouracil