Synthesis and biological evaluation of phosphoramidate prodrugs of two analogues of 2-deoxy-d-ribose-1-phosphate directed to the discovery of two carbasugars as new potential anti-HIV leads.

Nadège Hamon, Magdalena Slusarczyk, Michaela Serpi, Jan Balzarini, Christopher McGuigan

Bioorganic & medicinal chemistry 2014 Dec 25

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2-Deoxy-α-d-ribose-1-phosphate is of great interest as it is involved in the biosynthesis and/or catabolic degradation of several nucleoside analogues of biological and therapeutic relevance. However due to the lack of a stabilising group at its 2-position, it is difficult to synthesize stable prodrugs of this compound. In order to overcome this lack of stability, the synthesis of carbasugar analogues of 2-deoxyribose-1-phosphate was envisioned. Herein the preparation of a series of prodrugs of two carbocyclic analogues of 2-deoxyribose-1-phosphate using the phosphoramidate ProTide technology, along with their biological evaluation against HIV and cancer cell proliferation, is reported. Copyright © 2014 Elsevier Ltd. All rights reserved.

Citation

Nadège Hamon, Magdalena Slusarczyk, Michaela Serpi, Jan Balzarini, Christopher McGuigan. Synthesis and biological evaluation of phosphoramidate prodrugs of two analogues of 2-deoxy-d-ribose-1-phosphate directed to the discovery of two carbasugars as new potential anti-HIV leads. Bioorganic & medicinal chemistry. 2014 Dec 25;23(4):829-38