Synthesis of 3'-o-phosphonoethyl nucleosides with an adenine and a thymine base moiety.
The synthesis and antiviral evaluation of new 3'-O-phosphonoethyl modified phosphonate nucleosides related to PMDTA and PMDTT is described. The reaction scheme starts from protected L-threose and the phosphonate group is introduced by the Arbuzov reaction. The 2'-OH as well as the 2'-deoxygenated nucleosides have been obtained. Unfortunately, none of these synthesized compounds shows activity against HIV and HCV.
Huang
Qiuya
Q
Laboratory of Medicinal Chemistry, Rega Institute for Medical Research, K.U. Leuven, Leuven, Belgium.
Herdewijn
Piet
P
D000225:Adenine / Q000737:chemistry*; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D002460:Cell Line; D002470:Cell Survival; D006678:HIV / Q000187:drug effects; D016174:Hepacivirus / Q000187:drug effects; D006801:Humans; D008826:Microbial Sensitivity Tests; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry*; D063065:Organophosphonates / Q000737:chemistry*; D013941:Thymine / Q000737:chemistry*
D000998:Antiviral Agents; D009705:Nucleosides; D063065:Organophosphonates; D000225:Adenine; D013941:Thymine