首页> 外文期刊>Current Protocols in Nucleic Acid Chemistry >Synthesis of 9-(6-Deoxy-a-L-Talofuranosyl)-6-Methylpurine and 9-(6-Deoxy-P-D-Allofuranosyl)-6-Methylpurine Nucleosides
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Synthesis of 9-(6-Deoxy-a-L-Talofuranosyl)-6-Methylpurine and 9-(6-Deoxy-P-D-Allofuranosyl)-6-Methylpurine Nucleosides

机译:的合成(9) - 6-Deoxy-a-L-Talofuranosyl 6-methylpurine和(9) - 6-Deoxy-P-D-Allofuranosyl 6-methylpurine核苷

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摘要

6-Methylpurine (MeP) is a cytotoxic adenine analog that does not exhibit selectivity when administered systemically and could be very useful in a gene therapy approach to cancer treatment involving Escherichia coli purine nucleoside phosphorylase (PNP). 9-(6-Deoxy-P-D-allofuranosyl)-6-methylpurine [methyl(allo)-MePR, 18] and 9-(6-deoxy-a-L-talofuranosyl)-6-methylpurine [methyl(talo)-MePR, 21] were synthesized as potential prodrugs for MeP in the E. coli PNP/prodrug cancer gene therapy approach. The detailed syntheses of [methyl(allo)-MePR] and [methyl(talo)-MePR] are described. The glycosyl donors, 1,2-di-0-acetyl-3,5-di-0-benzyl-a-D-allofuranose (12) and 1-O-acetyl-3-O-benzyl-2,5-di-O-benzoyl-a-L-talofuranose (16) were prepared from 1,2:5,6-di-0-isopropylidene-a-D-glucofuranose (4) in nine and eleven steps, respectively. Vorbruggen coupling of the latter glycosyl donors with 6-methylpurine (3), followed by deprotection of the sugar hydroxyl groups, gave the title compounds in good overall yields.
机译:6-Methylpurine (MeP)是一种细胞毒性腺嘌呤模拟这并不表现出选择性的时候管理系统,可以非常有用的基因治疗癌症的方法治疗包括大肠杆菌嘌呤核苷磷酸化酶(PNP)。(9) - 6-Deoxy-P-D-allofuranosyl 6-methylpurine[methyl () -MePR、18]和(9) - 6-deoxy-a-L-talofuranosyl 6-methylpurine(甲基(talo)万众瞩目,21)合成潜在高活性化合物对大肠杆菌的议员PNP /前体药物癌症基因治疗的方法。详细的合成甲基(喂)万众瞩目和(甲基(talo)荣)。捐助者、1、2-di-0-acetyl-3 5-di-0-benzyl-a-D-allofuranose(12)和

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