高等学校化学学报

高等学校化学学报 ›› 2013, Vol. 34 ›› Issue (5): 1143.doi: 10.7503/cjcu20120954

• 有机化学 • 上一篇    下一篇

新型S(N)-β-D-葡萄糖苷-4-N-(取代邻羟苯基)亚胺基-5-(4-甲基-1,2,3-噻二唑)-1,2,4-三唑的合成及生物活性

冯钟念, 卢俊瑞, 辛春伟, 李建发, 鲍秀荣, 张彤彤   

  1. 天津理工大学化学化工学院, 天津 300384
  • 收稿日期:2012-10-22 出版日期:2013-05-10 发布日期:2013-05-10
  • 通讯作者: 卢俊瑞, 男, 教授, 博士生导师, 主要从事新型精细化学品研究. E-mail: lujunrui@tjut.edu.cn E-mail:lujunrui@tjut.edu.cn
  • 基金资助:

    国家自然科学基金(批准号: 21176194, 20976135)资助.

Synthesis of Novel S(N)-β-D-Glucosides of 4-N-(Substituted- 2-hydroxyphenyl)-imino-5-(4-methyl-1,2,3-thiadiazol-5-yl)-2H-1,2,4-triazole-3-thiones and Their Antibacterial Activities

FENG Zhong-Nian, LU Jun-Rui, XIN Chun-Wei, LI Jian-Fa, BAO Xiu-Rong, ZHANG Tong-Tong   

  1. School of Chemistry and Chemical Engineering, Tianjin University of Technology, Tianjin 300384, China
  • Received:2012-10-22 Online:2013-05-10 Published:2013-05-10

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摘要：

在KOH/acetone体系中, 4-N-(取代邻羟苯基)亚胺基-5-(4-甲基-1,2,3-噻二唑)-1,2,4-三唑-3-硫酮(3a～3d)与溴-α-D-四乙酰葡萄糖发生Kenigs-Knorr反应, 合成了8个未见报道的S(N)-β-D-乙酰葡萄糖苷, 其结构经1H NMR、 13C NMR、 红外光谱及元素分析等确定. 目标化合物的生物活性测试结果表明, 它们对金黄色葡萄球菌、 白色念珠菌和大肠杆菌均显示了较好的抑菌活性, 其效果接近或优于对照药物三氯生和氟康唑的抑菌效能. 其中, 化合物2-N-(2',3',4',6'-O-四乙酰基-β-D-吡喃葡萄糖基)-4-N-(3,5-二溴邻羟苯基)亚胺基-5-(4-甲基-1,2,3-噻二唑)-1,2,4-三唑-3-硫酮(4d)及3-S-(2',3',4',6'-O-四乙酰基-β-D-吡喃葡萄糖硫基)-4-N-(3,5-二溴邻羟苯基)亚胺基-5-(4-甲基-1,2,3-噻二唑)-1,2,4-三唑(5d)具有较强的抑菌活性.

关键词: 1,2,4-三唑, 糖苷, 合成, 生物活性

Abstract:

Eight novel S(N)-β-D-glucosides were synthesized by glycosylation of 4-N-(substituted-2-hydroxyphenyl)-imino-5-(4-methyl-1,2,3-thiadiazol-5-yl)-2H-1,2,4-triazole-3-thiones(3a—3d) with bromo-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside in acetone in the presence of potassium hydroxide. The structures of all compounds were confirmed by IR, 1H NMR and 13C NMR spectra. The preliminary bioassay showed that all target compounds possessed efficient antibacterial activities on Staphylococcus aureus, Monilia albican and Escherichia coli, which is close to or better than the controlled drugs(triclosan and fluconazole). Especially the compounds 2-N-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-4-N-(3,5-dibromo-2-hydroxyphenyl)-imino-5-(4-methyl-1,2,3-thiadiazol-5-yl)-1,2,4-triazole-3-thione(4d) and 3-S-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl-thio)-4-N-(3,5-dibromo-2-hydroxyphenyl)-imino-5-(4-methyl-1,2,3-thiadiazol-5-yl)-4H-1,2,4-triazole(5d) have strong antibacterial activities in vitro.

Key words: 1,2,4-Triazole, Glucoside, Synthesis, Antibacterial

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