Substituted benzimidazoles: antiviral activity and synthesis of nucleosides

被引：40
作者：
Budow, Simone [1 ]
Kozlowska, Mariola [2 ]
Gorska, Agata [2 ]
Kazimierczuk, Zygmunt [2 ]
Eickmeier, Henning [3 ]
La Colla, Paolo [5 ]
Gosselin, Gilles [4 ]
Seela, Frank [1 ]
机构：
[1] Ctr Nanotechnol, Lab Bioorgan Chem & Chem Biol, Heisenbergstr 11, D-48149 Munster, Germany
[2] Warsaw Univ Life Sci, Inst Chem, PL-02787 Warsaw, Poland
[3] Univ Osnabruck, Inst Chem, Lab Chem 2, D-49069 Osnabruck, Germany
[4] Univ Montpellier 2, CNRS, Lab Cooperatif Idenix, Montpellier, France
[5] Univ Cagliari, Dipartimento Sci Tecnol Biomed, Cagliari, Italy
来源：
ARKIVOC | 2009年
关键词：
Benzimidazoles; L-nucleosides; antiviral screening; glycosylation; ANTIMICROBIAL ACTIVITY; HUMAN CYTOMEGALOVIRUS; INHIBITORS; POTENT; 2-TRIFLUOROMETHYLBENZIMIDAZOLES; GLYCOSYLATION; ANTIPROTOZOAL; CHEMISTRY; ANALOGS;
D O I：
10.3998/ark.5550190.0010.319
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The antiviral activity of a series of benzimidazole derivatives and substituted benzimidazole beta-L- and beta-D-2'-deoxyribonucleosides against selected RNA and DNA viruses including HIV-1, BVDV, YFV, DENV-2, WNV, HBV, HCV and human RSV was evaluated. In addition, the synthesis of several benzimidazole beta-L-2'-deoxyribonucleosides (1-4) and 2'-deoxy-2'-fluoro-beta-D-arabinofuranosyl nucleoside 5 is described. The stereoselective glycosylation of the anions of the functionalized benzimidazoles 6a, 12a and 28 with 3,5-di-O-(4-methylbenzoyl)-2-deoxy-alpha-L-erythro-pentofuranosyl chloride (29) furnished beta-L-2'-deoxyribonucleosides 1-4 while the glycosylation of the anion of 2-bromobenzimidazole (12a) with 3,5-di-O-benzoyl-2-deoxy-2-fluoro-alpha-D-arabinofuranosyl bromide 34 gave the 2'-deoxy-2-fluoro-beta-D-arabinofuranosyl nucleoside 5. Moreover, the crystal structure of the benzoylated 2-bromobenzimidazole 2'-deoxy-2'-fluoro-beta-D-arabinofuranosyl nucleoside 35 is reported.
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收藏
页码：225 / 250
页数：26
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