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5-氨基-1-(5-脱氧-β-D-呋喃核糖基)咪唑-4-甲酰胺及相关5'-脱氧咪唑核糖核苷的合成

Synthesis of 5-amino-1-(5-deoxy-beta-D-ribofuranosyl)imidazole-4-carboxamide and related 5'-deoxyimidazole ribonucleosides.

作者信息

Srivastava P C, Newman A R, Matthews T R, Robins R K

出版信息

J Med Chem. 1975 Dec;18(12):1237-40. doi: 10.1021/jm00246a013.

DOI:10.1021/jm00246a013
PMID:172632
Abstract

5-Amino-1-(beta-D-ribofuranosyl)imidazole-4-carboxamide (1, AICA ribonucleoside) was converted in two steps to 5-amino-1-(5-deoxy-5-iodo-2,3-O-isopropylidene-beta-D-ribofuranosyl)imidazole-4-carboxamide (3) which was hydrogenated in the presence of Pd/C to yield 5-amino-1-(5-deoxy-2,3-O-isopropylidene-beta-D-ribofuranosyl)imidazole-4-carboxamide (4). The dehydration of 4 yielded 5-amino-1-(5-deoxy-2,3-O-isopropylidene-beta-D-ribofuranosyl)imidazole-4-carbonitrile (7). The compounds 3, 4, and 7 were deblocked with formic acid to furnish 5-amino-1-(5-deoxy-5-iodo-beta-D-ribofuranosyl)imidazole-4-carboxamide (6). 5-amino-1-(5-deoxy-beta-D-ribofuranosyl)imidazole-4-carboxamide (5), and 5-amino-1-(5-deoxy-beta-D-ribofuranosyl)imidazole-4-carbonitrile (8), respectively. Compound 8 was acetylated and then deaminated to give 1-(2,3-di-O-acetyl-5-deoxy-beta-D-ribofuranosyl)imidazole-4-carbonitrile (11). The compounds 8 and 11 were converted into 5-amino-1-(5-deoxy-beta-D-ribofuranosyl)imidazole-4-thiocarboxamide (9) and 1-(5-deoxy-beta-D-ribofuranosyl)imidazole-4-thiocarboxamide (12), respectively. The synthesis of 1-(5-deoxy-beta-D-ribofuranosyl)imidazole-4-carboxamide (13) was achieved for the first time by the treatment of 11 with hydrogen peroxide in the presence of ammonium hydroxide. The compounds were tested for antibacterial, antifungal, and antiviral activity, with 5 and 6 significantly inhibitory to Staphylococcus aureus.

摘要

5-氨基-1-(β-D-呋喃核糖基)咪唑-4-甲酰胺（1，AICA核苷）分两步转化为5-氨基-1-(5-脱氧-5-碘-2,3-O-异亚丙基-β-D-呋喃核糖基)咪唑-4-甲酰胺（3），3在钯/碳存在下氢化生成5-氨基-1-(5-脱氧-2,3-O-异亚丙基-β-D-呋喃核糖基)咪唑-4-甲酰胺（4）。4脱水生成5-氨基-1-(5-脱氧-2,3-O-异亚丙基-β-D-呋喃核糖基)咪唑-4-腈（7）。化合物3、4和7用甲酸脱保护，分别得到5-氨基-1-(5-脱氧-5-碘-β-D-呋喃核糖基)咪唑-4-甲酰胺（6）、5-氨基-1-(5-脱氧-β-D-呋喃核糖基)咪唑-4-甲酰胺（5）和5-氨基-1-(5-脱氧-β-D-呋喃核糖基)咪唑-4-腈（8）。化合物8乙酰化后脱氨基得到1-(2,3-二-O-乙酰基-5-脱氧-β-D-呋喃核糖基)咪唑-4-腈（11）。化合物8和11分别转化为5-氨基-1-(5-脱氧-β-D-呋喃核糖基)咪唑-4-硫代甲酰胺（9）和1-(5-脱氧-β-D-呋喃核糖基)咪唑-4-硫代甲酰胺（12）。1-(5-脱氧-β-D-呋喃核糖基)咪唑-4-甲酰胺（13）的合成首次通过在氢氧化铵存在下用过氧化氢处理11实现。对这些化合物进行了抗菌、抗真菌和抗病毒活性测试，其中5和6对金黄色葡萄球菌有显著抑制作用。

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