Recent advances in the synthesis of confortnationally locked nucleosides and their success in probing the critical question of conformational preferences by their biological targets

被引:33
作者
Choi, Y [1 ]
Moon, HR [1 ]
Yoshimura, V [1 ]
Marquez, VE [1 ]
机构
[1] NCI, Med Chem Lab, Ctr Canc Res, NIH,HHS, Frederick, MD 21702 USA
关键词
bicyclo[3.1.0]hexane and bicyclo[3.1.0]hexene; conformationally locked carbocyclic nucleosides; pseudorotational analysis; D4T and carbovir analogues; intramolecular cyclopropanation; lipase-catalyzed resolution;
D O I
10.1081/NCN-120021954
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The present work describes some recent approaches to the syntheses of three classes of locked-North nucleosides: beta-D-ribo-, beta-D-deoxyribo-, and beta-D-dideoxy-ribonucleosides. The method developed for the latter class permitted access to a novel bicyclo[3.1.0]hexene-type nucleosides structurally similar to D4T and carbovir. A structural analysis and biological activities are discussed.
引用
收藏
页码:547 / 557
页数:11
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