Acyclic nucleosides: Synthesis of 1-[(1-hydroxy-2-propoxy)methyl]thymine, 6-azathymine, uracil, and 6-azauracil as potential antiviral agents

Article abstract of DOI:10.1080/15257779408011890

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).

Full text of DOI:10.1080/15257779408011890

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Nucleosides and Nucleotides
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Acyclic Nucleosides: Synthesis of 1-[(1-
Hydroxy-2-Propoxy) Methyl]Thymine, 6-
Azathymine, URACIL, AND 6-Azauracil as
Potential Antiviral Agents
Eng-Chi Wang a , Hour-Young Chen b & Cherng-Chyi Tzeng a
a School of Chemistry, Kaohsiung Medical College , Kaohsiung City,
807, Taiwan, Republic of China
b Division of Virology , National Institute of Preventive Medicine,
Nan-Kang , Taipei, Taiwan , 115, Republic of China
Published online: 24 Sep 2006.
To cite this article: Eng-Chi Wang , Hour-Young Chen & Cherng-Chyi Tzeng (1994) Acyclic
Nucleosides: Synthesis of 1-[(1-Hydroxy-2-Propoxy) Methyl]Thymine, 6-Azathymine, URACIL, AND
6-Azauracil as Potential Antiviral Agents, Nucleosides and Nucleotides, 13:5, 1201-1213, DOI:
10.1080/15257779408011890
To link to this article: http://dx.doi.org/10.1080/15257779408011890
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