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Design, synthesis, and biological evaluation of novel iso-d-2′,3′-dideoxy-3′-fluorothianucleoside derivatives

Title
Design, synthesis, and biological evaluation of novel iso-d-2′,3′-dideoxy-3′-fluorothianucleoside derivatives
Authors
Kim K.R.Moon H.R.Park A.-Y.Chun M.W.Jeong L.S.
Ewha Authors
정낙신
Issue Date
2007
Journal Title
Bioorganic and Medicinal Chemistry
ISSN
0968-0896JCR Link
Citation
vol. 15, no. 1, pp. 227 - 234
Indexed
SCI; SCIE; SCOPUS WOS scopus
Abstract
Novel iso-d-2′,3′-dideoxythianucleoside derivatives 1-4 were designed and asymmetrically synthesized as a bioisostere of lamivudine to search for new anti-HIV agents. The information about using sulfur participation occurred on DAST fluorination and Mitsunobu reaction will be of great help in synthesizing sulfur-containing compounds. Final compounds 1-4 were evaluated against HIV-1 and 2, HSV-1 and 2, EMCV, Cox. B3, VSV, FluA (Taiwan), FluA (Johan.), FCV, and FIP. Only cytosine analogue 3 showed a potent anti-VSV activity (EC50 = 9.43 μg/mL). This result implies that iso-2′,3′-dideoxy sugar templates might play a role of a sugar surrogate of nucleosides for the development of anti-RNA virus agent. © 2006 Elsevier Ltd. All rights reserved.
DOI
10.1016/j.bmc.2006.09.066
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약학대학 > 약학과 > Journal papers
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