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Synthesis and Anti‐HIV Activity of Guanine Modified Fluorinated Acyclic Nucleoside Phosphonate Derivatives
Authors:Min Luo,Elisabetta Groaz,Steven De&#x  Jonghe,Dominique Schols,Piet Herdewijn
Affiliation:Min Luo,Elisabetta Groaz,Steven De Jonghe,Dominique Schols,Piet Herdewijn
Abstract:The preparation of an unprecedented series of nucleobase modified 3‐fluoro‐2‐(phosphonomethoxy)propyl (FPMP) acyclic nucleosides in both their (R) and (S) enantiomerically pure forms is described. The synthesis focuses on a Mitsunobu alkylation reaction to construct the C?N(9) bond between a chiral fluorinated side‐chain residue and 6‐ or 7‐modified guanine analogs. Prodrugs of FPMP‐7‐deazaguanine were also synthesized by derivatization of the corresponding phosphonic acid functionality with (bis)diamyl aspartate amidate groups, leading to moderate activity against human immunodeficiency virus type 1 (HIV‐1).
Keywords:acyclic nucleoside phosphonates  Mitsunobu reaction, prodrugs  HIV  antiviral activity  cytotoxicity
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