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http://dx.doi.org/10.5012/bkcs.2008.29.9.1723

Synthesis and Anti-HIV-1 Activity of Carbocyclic Versions of Stavudine Analogues Using a Ring-closing Metathesis  

Liu, Lian-Jin (BK21-Project Team, College of Pharmacy, Chosun University)
Ko, Ok Hyun (BK21-Project Team, College of Pharmacy, Chosun University, Gwangju 501-759, Korea)
Hong, Joon-Hee (BK21-Project Team, College of Pharmacy, Chosun University)
Publication Information
Bulletin of the Korean Chemical Society / v.29, no.9, 2008 , pp. 1723-1728 More about this Journal
Abstract
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 ($EC_{50}$ = 11.91 $\mu$mol).
Keywords
Carbocyclic nucleoside; Antiviral agents; Ring-closing metathesis; Claisen rearrangement
Citations & Related Records
Times Cited By KSCI : 2  (Citation Analysis)
Times Cited By Web Of Science : 2  (Related Records In Web of Science)
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