Acyclic Nucleosides: Synthesis of 1-[(1-Hydroxy-2-Propoxy) Methyl]Thymine, 6-Azathymine, URACIL, AND 6-Azauracil as Potential Antiviral Agents
- 1 June 1994
- journal article
- research article
- Published by Taylor & Francis in Nucleosides and Nucleotides
- Vol. 13 (5) , 1201-1213
- https://doi.org/10.1080/15257779408011890
Abstract
A series of acyclic nucleosides have been synthesized. Thymine, 6-azathymine, uracil, and 6-azauracil were silylated with hexamethyldisilazane in the presence of ammonium sulfate and then coupled with 1-benzyloxy-2-chloromethoxypropane to give the corresponding 1-(1-benzyloxy-2-propoxy)methyl derivatives. A minor quantity of benzyloxymethylated product was also obtained in each case. Hydrogenolysis of the protected acyclic nucleosides with palladium(II) hydroxide afforded the title compounds. None of the compounds exhibited significant antiviral activity against human immunodeficiency virus (HIV).Keywords
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