Synthesis and anti-HIV evaluation of new acyclic phosphonate nucleotide analogues and their bis(SATE) derivatives.
This article describes a very simple route for synthesizing novel lipophilic phosphonate bis(t-bu-SATE) prodrugs of acyclic cyclopentenylated nucleosides such as adenine 17 and cytosine 18. The key intermediate 6 was constructed via a ring-closing metathesis of compound 5, which could be readily prepared from diethylmalonate 4. The chemical stability of the bis(SATE) derivatives was tested at neutral (pH = 7.2) and slightly acid (milli-Q water, pH = 5.5) pH. The synthesized compounds were evaluated as potential antiviral agents against HIV-1 virus.
Li
Hua
H
BK-21 Project Team, College of Pharmacy, Chosun University, Kwangju, Republic of Korea.
Hong
Joon Hee
JH
D000144:Acids, Acyclic / Q000737:chemistry*; D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015497:HIV-1 / Q000187:drug effects*; D006863:Hydrogen-Ion Concentration; D008314:Malonates / Q000737:chemistry; D015394:Molecular Structure; D009705:Nucleosides / Q000737:chemistry*; D063065:Organophosphonates / Q000737:chemistry*; D011355:Prodrugs / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
D000144:Acids, Acyclic; D019380:Anti-HIV Agents; D008314:Malonates; D009705:Nucleosides; D063065:Organophosphonates; D011355:Prodrugs; C498810:diethyl malonate