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

被引：6
作者：
Choi, Won Jun [1 ,2 ,3 ]
Ko, Yun Jung [1 ,2 ]
Chandra, Girish [1 ,2 ]
Lee, Hyuk Woo [1 ,2 ]
Kim, Hea Ok [1 ,2 ]
Koh, Hyo Jung [1 ,2 ]
Moon, Hyung Ryong [4 ]
Jung, Young Hoon [5 ]
Jeong, Lak Shin [1 ,2 ]
机构：
[1] Ewha Womans Univ, Coll Pharm, Dept Bioinspired Sci, Seoul 120750, South Korea
[2] Ewha Womans Univ, Coll Pharm, Med Chem Lab, Seoul 120750, South Korea
[3] Dongguk Univ, Coll Pharm, Kyonggi Do 410774, South Korea
[4] Pusan Natl Univ, Coll Pharm, Pusan 609753, South Korea
[5] Sungkyunkwan Univ, Sch Pharm, Suwon 440746, South Korea
来源：
TETRAHEDRON | 2012年 / 68卷 / 04期
基金：
美国国家科学基金会;
关键词：
Stereoselective epoxidation; Cyclic sulfate; Sulfur ylide; Carbocyclic nucleosides; Anti-HCV activity; C-13; MAGNETIC-RESONANCE; HEPATITIS-C; CARBOCYCLIC NUCLEOSIDES; CYCLIC SULFATES; RIBONUCLEOSIDES; DISCRIMINATE; POLYMERASE; INHIBITOR; CHEMISTRY; DISCOVERY;
D O I：
10.1016/j.tet.2011.11.052
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1253 / 1261
页数：9
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