(+/-)-CARBOCYCLIC 5'-NOR-2'-DEOXYGUANOSINE AND RELATED PURINE DERIVATIVES - SYNTHESIS AND ANTIVIRAL PROPERTIES

被引：28

作者：

PATIL, SD

KOGA, M

SCHNELLER, SW

SNOECK, R

DECLERCQ, E

机构：

[1] UNIV S FLORIDA,DEPT CHEM,TAMPA,FL 33620

[2] CATHOLIC UNIV LEUVEN,REGA INST MED RES,B-3000 LOUVAIN,BELGIUM

来源：

JOURNAL OF MEDICINAL CHEMISTRY | 1992年 / 35卷 / 12期

关键词：

D O I：

10.1021/jm00090a007

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Beginning with 3-cyclopenten-1-ylamine hydrochloride, the 5'-nor derivatives of carbocyclic 2'-deoxyguanosine (2), 2'-deoxyadenosine (3), and 2,6-diaminopurine 2'-deoxyribofuranoside (4) have been prepared. These compounds were evaluated for antiviral potential versus herpes simplex virus, varicella-zoster virus, cytomegalovirus, vaccinia virus, vesicular stomatitis virus, and human immunodeficiency virus and found to lack activity. Also, compounds 2-4 were virtually nontoxic toward the host (human diploid fibroblast ESM and HEL) cells. These biological properties may be due to the inability of 2-4 to be phosphorylated to the requisite nucleotide level that is likely to be necessary for biological activity by correlation to carbocyclic 2'-deoxyguanosine (1), which possesses significant antiviral properties as a result of conversion to its 5'-triphosphate derivative.

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页码：2191 / 2195

页数：5

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