NOVEL ISOMERIC DIDEOXYNUCLEOSIDES AS POTENTIAL ANTIVIRAL AGENTS

被引：67

作者：

BOLON, PJ ^{[1
]}

SELLS, TB ^{[1
]}

NUESCA, ZM ^{[1
]}

PURDY, DF ^{[1
]}

NAIR, V ^{[1
]}

机构：

[1] UNIV IOWA,DEPT CHEM,IOWA CITY,IA 52242

来源：

TETRAHEDRON | 1994年 / 50卷 / 26期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4020(01)85259-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel isomeric dideoxynucleosides with S,S absolute stereochemistry and involving the transposition of the base moiety from the normal 1'- to the 2'-position have been regiospecifically and stereospecifically synthesized. The synthetic approaches involved either direct coupling with inversion at the 2-position of a preformed dideoxygenated sugar using the base moiety as nucleophile (for purine isodideoxynucleosides) or construction of the base moiety onto a stereochemically defined amino sugar precursor (pyrimidine isodideoxynucleosides). These compounds possess extremely high stability with respect to ''glycosidic'' bond cleavage and enzymatic deamination. Antiviral data suggest that the most active compound was levorotatory S,S-isodideoxyadenosine.

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页码：7747 / 7764

页数：18

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