4-巯基嘧啶的一些S-β-D-葡萄糖苷的合成及其抗菌活性
Synthesis and antimicrobial activity of some S-beta-D-glucosides of 4-mercaptopyrimidine.
作者信息
Moustafa A H, Morsy H A, Assy M G, Haikal A Z
机构信息
Department of Chemistry, Faculty of Science, Zagazig University, Zagazig, Egypt. ah hu
出版信息
Nucleosides Nucleotides Nucleic Acids. 2009 Sep;28(9):835-45. doi: 10.1080/15257770903172639.
5-Acetyl-2-aryl-6-methyl-4-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosylmercapto)pyramidines 3a-c were obtained by the reaction of 5-acetyl-2-aryl-6-methyl-pyrimidine thiol 1a-c with 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide (2) in aq. KOH/acetone. The reaction of 1a-c with peracetylated galactose 5 and peracetylated ribose 8 under MW irradiation gave 5-acetyl-2-aryl-6-methyl-4-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosylmercapto)pyrimidine 6a-c and 5-acetyl-2-aryl-6-methyl-4-(2,3,5-tri-O-acetyl-beta-D-ribofuranosylmercapto)pyrimidines 9a-c. The deprotection of 3a-c, 6a-c, and 9a-c in the presence of methanol and TEA/H(2)O yielded the deprotected products 4a-c, 7a-c, and 10a-c. The structures of the compounds were confirmed by using IR, (1)H, (13)C spectra and microanalysis. Selected members of these compounds were screened for antimicrobial activity.
通过5-乙酰基-2-芳基-6-甲基嘧啶硫醇1a-c与2,3,4,6-四-O-乙酰基-α-D-吡喃葡萄糖基溴（2）在氢氧化钾水溶液/丙酮中反应，得到5-乙酰基-2-芳基-6-甲基-4-(2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖基巯基)嘧啶3a-c。1a-c与全乙酰化半乳糖5和全乙酰化核糖8在微波辐射下反应，得到5-乙酰基-2-芳基-6-甲基-4-(2,3,4,6-四-O-乙酰基-β-D-吡喃半乳糖基巯基)嘧啶6a-c和5-乙酰基-2-芳基-6-甲基-4-(2,3,5-三-O-乙酰基-β-D-呋喃核糖基巯基)嘧啶9a-c。3a-c、6a-c和9a-c在甲醇和三乙胺/水存在下脱保护，得到脱保护产物4a-c、7a-c和10a-c。通过红外光谱、¹H、¹³C光谱和微量分析确定了这些化合物的结构。对这些化合物的选定成员进行了抗菌活性筛选。
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