Synthesis of 3′- O -Phosphonoethyl Nucleosides with an Adenine and a Thymine Base Moiety
2009; Taylor & Francis; Volume: 28; Issue: 5-7 Linguagem: Inglês
10.1080/15257770903044184
ISSN1532-2335
Autores Tópico(s)Synthesis and Characterization of Heterocyclic Compounds
ResumoAbstract 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. Keywords: Phosphonate nucleosidesPMDTAPMDTTArbuzov reaction Acknowledgments This article is dedicated to Dr. Robins on his 70th birthday. The authors are indebted to Dr. R. L. Mackman (Gilead Sciences) for helpful discussions and for providing the antiviral data and to Gilead Sciences for the financial support. Notes aEC50 = 50% effective concentration, or concentration required to protect 50% of the cells against viral cytopathicity. bCC50 = 50% cytotoxic concentration, or concentration reducing the number of viable cells by 50%.
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