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DOI: 10.1055/s-0030-1258397
Novel 5-(N-Alkylaminouracil) Acyclic Nucleosides
Publikationsverlauf
Publikationsdatum:
12. Januar 2011 (online)
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Abstract
Protocols for the two-step syntheses of new 5-(N-hydroxyalkyl- and 5-N-benzylamino)uracil acyclic nucleosides bearing various functional groups (alkoxy/hydroxy and cyano/ester) are presented. Two groups of the title compounds were synthesised via aminolysis of 5-bromouracil and, subsequently, either coupling with an alkylating agent (2-chloromethoxyethyl acetate), or Michael-type addition to acrylonitrile/methyl acrylate. The reverse sequences for both syntheses were also studied. The target molecules were designed as non-nucleoside reverse transcriptase inhibitors (NNRTI) and are analogues of 1-(hydroxyethoxymethyl)-6-thiophenylthymine (HEPT) and 3-benzyl-1-cyanomethyluracils. The obtained compounds will be used in screening tests for anti-HIV-1 activity.
Key words
acyclic nucleosides - 5-(N-alkylamino)uracil - aminolysis - N-alkylation - Michael-type addition
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