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. Georg Thieme Verlag Stuttgart New York.
Boncel, Sawomir,Gondela, Andrzej,McZka, MacIej,Tuszkiewicz-Kuznik, Magdalena,Grec, Przemysaw,Hefczyc, Barbara,Walczak, Krzysztof
experimental part
p. 603 - 610
(2011/04/12)
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