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  • Title: S-acyl-2-thioethyl phosphoramidate diester derivatives as mononucleotide prodrugs.
    Author: Egron D, Imbach JL, Gosselin G, Aubertin AM, Périgaud C.
    Journal: J Med Chem; 2003 Oct 09; 46(21):4564-71. PubMed ID: 14521418.
    Abstract:
    The synthesis and in vitro anti-HIV activity of phosphoramidate diester derivatives of 3'-azido-2',3'-dideoxythymidine (AZT) bearing one S-pivaloyl-2-thioethyl (tBuSATE) group and various amino residues are reported. These compounds were obtained from an H-phosphonate strategy using an amidative oxidation step. Most of these derivatives appeared to inhibit HIV-1 replication, with EC(50) values at micromolar concentration in thymidine kinase-deficient (TK-) cells, revealing a less restrictive intracellular decomposition process than previously reported for other phosphoramidate prodrugs. The proposed decomposition pathway of this new series of mixed pronucleotides may successively involve an esterase and a phosphoramidase hydrolysis.
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