Synthesis and antiviral evaluation of certain novel pyrazinoic acid C-nucleosides.
Synthesis and antiviral evaluation of certain novel pyrazinoic acid C-nucleosides.
复制标题
某些新型吡嗪酸C-核苷的合成和抗病毒评价。
DOI：
10.1021/jm970532z
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发表时间：
1998
期刊：
影响因子：
--
通讯作者：
Townsend,LB
中科院分区：
文献类型：
--
作者：
Walker2nd,JA;Liu,W;Wise,DS;Drach,JC;Townsend,LB
Pyrazine (1,4-diazine)C-nucleosides constitute a rare class of nucleic acid analogues that has only recently been reported in the literature. As part of our ongoing investigation into the synthesis and reactivity of these compounds, we have developed an electrophilic esterification of a lithiated pyrazineC-nucleoside (1) to give, following deprotection, the versatile intermediate ethyl 3,5-dichloro-6-(β-d-ribofuranosyl)pyrazine-2-carboxylate (4). This intermediate was subjected to a variety of reaction conditions to generate a series of pyrazinoic acidC-nucleosides. These compounds, along with 3,5-dichloro-2-(β-d-ribofuranosyl)pyrazine (2) and4, were evaluated for antiviral activity and cytotoxicity. No significant activity was observed for compounds2and5−9, but4was active against two herpes viruses and cytotoxic in the micromolar range.
