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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 29, Number 9
BKCSDE 29(9)
September 20, 2008 

Synthesis and Anti-HIV-1 Activity of Carbocyclic Versions of Stavudine Analogues Using a Ring-closing Metathesis
Lian Jin Liu, Ok Hyun Ko, Joon Hee Hong*
Carbocyclic nucleoside, Antiviral agents, Ring-closing metathesis, Claisen rearrangement
An efficient synthetic route for carbocyclic versions of stavudine analogues and their evaluation on antiviral activity are described. The construction of an ethynylated quaternary carbon at the 4'-position of carbocyclic nucleosides was accomplished using Claisen rearrangement of 11 and ring-closing metathesis (RCM) of dienyne 14 as key transformations. An antiviral evaluation of the synthesized compounds, 20, 21, 22, and 25 against HIV-1, HSV-1, HSV-2, and HCMV showed that only the guanine analogue 25 is moderately active against HIV-1 in the MT-4 cell line (EC50 = 11.91 μmol).
1723 - 1728
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