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Stereoselective synthesis and anti-HCV activity of conformationally restricted 2′-C-substituted carbanucleosides

Title
Stereoselective synthesis and anti-HCV activity of conformationally restricted 2′-C-substituted carbanucleosides
Authors
Choi W.J.Ko Y.J.Chandra G.Lee H.W.Kim H.O.Koh H.J.Moon H.R.Jung Y.H.Jeong L.S.
Ewha Authors
정낙신최원준
Issue Date
2012
Journal Title
Tetrahedron
ISSN
0040-4020JCR Link
Citation
vol. 68, no. 4, pp. 1253 - 1261
Indexed
SCI; SCIE; SCOPUS WOS scopus
Abstract
Conformationally restricted 2′-C-azido-, hydroxy- and fluoromethyl-carbanucleosides 4b-f were efficiently synthesized via the stereoselective conversion of ketone 7 to epoxide 14, followed by the stereoselective opening of the epoxide with nucleophiles (OAc, N 3, and F), while the corresponding 2′-C-methyl-carbanucleoside 4a was synthesized via the stereoselective Grignard reaction of ketone 7 with methylmagnesium iodide as a key step. All the final nucleosides 4a-f were assayed for anti-HCV activity, but showed neither significant anti-HCV activity nor cytotoxicity in a cell-based replicon assay. © 2011 Elsevier Ltd. All rights reserved.
DOI
10.1016/j.tet.2011.11.052
Appears in Collections:
약학대학 > 약학과 > Journal papers
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