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Aryl nucleoside H-phosphonates. Part 16: synthesis and anti-HIV-1 activity of di-aryl nucleoside phosphotriesters. 2009
Joanna Romanowska, and
Agnieszka Szymańska-Michalak, and
Jerzy Boryski, and
Jacek Stawiński, and
Adam Kraszewski, and
Roberta Loddo, and
Giuseppina Sanna, and
Gabriella Collu, and
Barbara Secci, and
Paolo La Colla
Institute of Bioorganic Chemistry, Polish Academy of Sciences, Poznań, Poland.
Di-aryl nucleoside phosphotriesters have been explored as a new type of pronucleotides for the purpose of anti-HIV-1 therapy and efficient synthetic protocols, based on H-phosphonate chemistry, have been developed for the preparation of this class of compounds. It was found that anti-HIV-1 activity of the phosphotriesters bearing an antiviral nucleoside moiety (AZT, ddA) and also ddU was due, at least partially, to intracellular conversion into the corresponding nucleoside 5'-monophosphates, and their efficiency correlated well with the pK(a) values of the aryloxy groups present.
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