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Aryl H-phosphonates 17: (N-aryl)phosphoramidates of pyrimidine nucleoside analogues and their synthesis, selected properties, and anti-HIV activity. 2011
Joanna Romanowska, and
Michał Sobkowski, and
Agnieszka Szymańska-Michalak, and
Krystian Kołodziej, and
Aleksandra Dąbrowska, and
Andrzej Lipniacki, and
Andrzej Piasek, and
Zofia M Pietrusiewicz, and
Marek Figlerowicz, and
Andrzej Guranowski, and
Jerzy Boryski, and
Jacek Stawiński, and
Adam Kraszewski
Institute of Bioorganic Chemistry, Polish Academy of Sciences, Noskowskiego 12/14, 61-704 Poznań, Poland.
New synthetic protocol for the preparation of nucleoside 5'-(N-aryl)phosphoramidate monoesters 4 was developed. It consisted of a condensation of the corresponding nucleoside 5'-H-phosphonates with aromatic- or heteroaromatic amines promoted by diphenyl phosphorochloridate, followed by oxidation of the produced H-phosphonamidates with iodine/water. 5'-(N-Aryl)phosphoramidate monoesters derived from 3'-azido-3'-deoxythymidine (AZT) or 2',3'-dideoxyuridine (ddU) nucleosides and various aromatic and heteroaromatic amines were evaluated as potential anti-HIV drugs. It was found that these compounds act most likely as pronucleotides and that some of them have therapeutic indices superior to those of the reference AZT.
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