Synthesis and in vitro evaluation of S-acyl-3-thiopropyl prodrugs of Foscarnet

…, G Gosselin, C Pannecouque, E De Clercq

Index: Gagnard, Valerie; Leydet, Alain; Morere, Alain; Montero, Jean-Louis; Lefebvre, Isabelle; Gosselin, Gilles; Pannecouque, Christophe; De Clercq, Erick Bioorganic and Medicinal Chemistry, 2004 , vol. 12, # 6 p. 1393 - 1402

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Citation Number: 13

Abstract

A new enzyme-labile group called S-acyl-3-thiopropyl group (SATP) has been synthesized from allylic esters of phosphonate. After demonstration of the enzyme-labile character of the SATP in cellular extracts, it has been introduced onto the phosphonate moiety of PFA (Foscarnet) to obtain potential lipophilic prodrugs. To ponder the lipophilicity of the triesters of PFA, esters of monomethylether of polyethyleneglycols and of thioglycerol were ...