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Sugar modified pyrimido[4,5-b]indole nucleosides: synthesis and antiviral activity
RSC Medicinal Chemistry ( IF 4.1 ) Pub Date : 2017-08-25 00:00:00 , DOI: 10.1039/c7md00319f
Juraj Konč 1, 2, 3, 4 , Michal Tichý 1, 2, 3, 4 , Radek Pohl 1, 2, 3, 4 , Jan Hodek 1, 2, 3, 4 , Petr Džubák 4, 5, 6, 7, 8 , Marián Hajdúch 4, 5, 6, 7, 8 , Michal Hocek 1, 2, 3, 4, 9
Affiliation  

Three types of sugar modified pyrimido[4,5-b]indole nucleosides (2′-deoxy-2′-fluororibo-, 2′-deoxy-2′-fluoroarabino- and arabinonucleosides) were synthesized by glycosylation of 4,6-dichloropyrimido[4,5-b]indole followed by modification of sugar moiety and introduction of substituents into position 4 by cross-coupling reactions or nucleophilic substitutions. Some 2′-fluororibo- and 2′-fluoroarabinonucleosides displayed interesting anti-HCV activities (IC50 = 1.6–20 μM) and the latter compounds also some anti-dengue activities (IC50 = 10.8–40 μM).

中文翻译:

糖修饰的嘧啶并[4,5- b ]吲哚核苷:合成与抗病毒活性

通过4,6-二氯嘧啶基的糖基化反应,合成了三种类型的糖修饰的嘧啶并[4,5- b ]吲哚核苷(2'-脱氧-2'-氟核糖-,2'-脱氧-2'-氟阿拉伯糖核苷和阿拉伯糖核苷)。 [4,5- b ]吲哚,其后修饰糖部分,并通过交叉偶联反应或亲核取代将取代基引入位置4。一些2'-氟核糖核苷和2'-氟阿拉伯糖核苷显示出有趣的抗HCV活性(IC 50 = 1.6–20μM),后一种化合物也具有一些抗登革热活性(IC 50 = 10.8–40μM)。
更新日期:2017-08-31
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