Syntheses, molecular structures, and antiviral activities of 1- and 2-(2鈥?deoxy-d-ribofuranosyl)cyclohepta[d][1,2,3]triazol-6(1H)-ones and 1-(2鈥?deoxy-d-ribofuranosyl)cyclohepta[b]pyrrol-8(1H)-one

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• 作者：Tomoo Nakazawa^a ; ^{tomoon@yamanashi.ac.jp} ; Takeshi Ohmae^a ; Masahiro Fujimuro^b ; Masahiko Ito^c ; Tohru Nishinaga^a ; Masahiko Iyoda^a ; ^{iyoda@tmu.ac.jp}
• 关键词：2&prime ; -Deoxyribofuranosides ; Cyclohepta[d][1 ; 2 ; 3]triazol-6(1H)-ones ; Cyclohepta[b]pyrrol-8(1H)-ones ; Glycosylation ; X-ray structures
• 刊名：Tetrahedron
• 出版年：2012
• 期刊代码：107_00404020
• 类别：ch
• 出版时间：8 July, 2012
• 卷：68
• 期：27-28
• 页码：5368-5374
• 文件大小：552 K

摘要

The synthesis of a novel class of 2鈥?deoxyribonucleosides possessing tropone-fused nitrogen heterocycles as nucleobases was developed. The reaction of alkali metal salts of 1H-cyclohepta[d][1,2,3]triazol-6-one with 2-deoxy-3,5-di-O-(p-toluoyl)-伪-d-ribofuranosyl chloride (伪-chlorosugar) afforded an anomeric mixture of N1- and N2-coupled glycosylation products. Good stereospecificity in relation to the amount of the 尾-anomer was achieved in the less polar solvent DME. The reactions of the sodium salt of 1H-cyclohepta[b]pyrrol-8-one and its 3-methyl derivative with an 伪-chlorosugar in DME gave the 尾-anomer of the N1-coupled glycosylation products. The glycosylation products were treated with NaOMe in MeOH to produce the desired 2鈥?deoxyribonucleosides. X-ray structural analyses of the three nucleosides prepared confirmed their anomeric configuration and revealed that their sugars were puckered. The 尾-anomers of the nucleosides had weak antiviral activities for herpes simplex virus type 1 and herpes simplex virus type 2 in comparison with those of acyclovir (ACV). These nucleosides showed no cytotoxicity on a lung (A549) and two colon (HT-29 and HCT-116) cancer cell lines.