5-甲基-1,2,4-三唑-3-硫酮类糖苷化合物的合成及抗菌活性

Synthesis and Antibacterial Activities of 5-Methyl-1,2,4-triazole-3-thione Glucosides Compounds

在KOH/丙酮体系中,以5-甲基-4-N-取代苯基亚胺/胺基-1,2,4-三唑-3-硫酮为原料,与溴-α-D-四乙酰葡萄糖进行Kenigs-Knorr反应合成了10个新颖的化合物——5-甲基-4-N-取代苯基亚胺基/胺基-3-S-(2',3',4',6'-四-O-乙酰基-β-D-吡喃葡萄糖基)-1,2,4-三唑(2a^2e,5a^5e);并在二氯甲烷/甲醇/甲醇钠混合体系中水解脱除乙酰基,得到10个新颖的化合物——5-甲基-4-N-取代苯基亚胺基-3-S-(β-D-吡喃葡萄糖基)-1,2,4-三唑(3a^3e)及5-甲基-4-N-取代苯基胺基-3-S-(β-D-吡喃葡萄糖基)-1,2,4-三唑(6a^6e).化合物的结构均经核磁共振波谱(NMR)、红外光谱(IR)和高分辨质谱(HRMS)分析确证.生物活性测试结果表明,目标化合物对大肠杆菌、金黄色葡萄球菌、枯草芽孢杆菌和白色念珠球菌普遍具有较好的抗菌活性.化合物3d和3e对4种菌株的最小抑菌浓度相对较低,表现出较强的广谱抗菌活性.

Ten novel compounds of 5-methy-4- （ N-substituted-phenyl ） imino/amido-3-S- （ 2＇, 3＇, 4＇, 6 ＇-tetra-O-acetyl-β-D-glucopyranoside ） -1 5 -methy-4- （ N-substituted-phe ,2,4-triazole （2a-2e and 5a-5e ） were synthesized via glycosylation of ） imino/amido-1,2,4-triazole-3-thiones with bromo-2,3,4,6-tetra-O-acetyl- β-D-glucopyranoside in acetone in the presence of potassium hydroxide. Subsequently, ten novel compounds of 5-methy-4- （ N-substituted-phenyl ） imino/amido-3-S- （β-D-Glucopyranosyl） -1,2,4-triazole （ 3a-3e and 6a- 6e） were generated by deacetylate reaction in the system of sodium methylate, methanol and dichloromethane. The structures of all compounds were confirmed by ^1H NMR, ^13C NMR, IR and HRMS spectra. The results of preliminary bioassay suggested that nearly all of the new compounds exerted variable inhibitory activity against Escherichia coli, Staphylococcus aureus, Bacillus subtilis and Monilia albican. Especially, compounds 3d and 3e had lower minimum inhibitory concentration values on four tested strains which showed the strong broadspectrum antimicrobial activity and great development potential.