Synthesis of novel 6-substituted acyclouridine derivatives and their anti-HIV-1 activity |
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Authors: | H Tanaka M Baba M Ubasawa H Takashima K Sekiya I Nitta R T Walker E De Clereq T Miyasaka |
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Affiliation: | School of Pharmaceutical Sciences, Showa University, Tokyo, Japan. |
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Abstract: | To improve the anti-HIV activity of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT), a variety of its analogues were synthesized. Introduction of SR group to the C-6 position was carried out based on LDA lithiation followed by the reaction of aryl- or alkyl disulfide. An addition-elimination reaction of a 6-phenylsulfinyl derivative was used for synthesizing the analogues having OR or NHR group at the C-6 position. The C-5 modified derivatives were synthesized mainly based on LTMP lithiation of a 6-phenylthio derivative. Modification at the 2- or 4-position was also carried out. Some compounds prepared in the present study showed higher activity than HEPT. |
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