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

发布时间：2018-01-02 15:13

本文关键词：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　出处：《高等学校化学学报》2016年02期 　论文类型：期刊论文

【摘要】：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.
[Abstract]:In the KOH/ acetone system, 5- methyl -4-N- phenyl imine / amine -1,2,4- three triazole thione -3- as raw materials, Kenigs-Knorr reaction with bromine alpha -D- four acetyl glucose 10 novel compounds - 5- methyl -4-N- phenyl imino / amine synthesis of -3-S- (2', 3', 4', 6'- four -O- acetyl beta -D- glucopyranosyl) -1,2,4- (2a~2e, 5a~5e) was three; and in methanol / dichloromethane / methanol mixture in the hydrolysis of sodium removal of acetyl, 10 new compounds of 5- methyl -4-N- substituted phenyl imino -3-S- (beta -D- glucopyranosyl) was three (3a~3e) and -1,2,4- 5- methyl -4-N- substituted phenyl amine -3-S- (beta -D- glucopyranosyl) -1,2,4- was three (6a~6e). The structure of compounds were confirmed by nuclear magnetic resonance spectroscopy (NMR), infrared spectroscopy (IR) and high resolution mass spectrometry (HRMS) analysis confirmed. Biological activity test results show that the target compounds of E. Bacilli, Staphylococcus aureus, Bacillus subtilis and Candida albicans generally have good antibacterial activity. Compounds 3D and 3E showed relatively strong minimum broad-spectrum antibacterial activity against the 4 strains.

【作者单位】：天津理工大学化学化工学院;
【基金】：国家自然科学基金(批准号:21176194;21476174)资助~~
【分类号】：O626.26
【正文快照】： 1,2,4-三唑类希夫碱衍生物具有消炎[1,2]、抗菌[3~5]及抗癌[6~8]等生物活性,因此一直是杂环化学研究领域的热点.研究[9]表明,含有卤素和芳环的1,2,4-三唑类希夫碱化合物的生物活性尤为突出.糖苷类药物具有水溶性好、化学性质稳定及抗菌谱广等特点[10],近年来已广泛应用于肿瘤

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