Synthesis of Novel D-Glucose-derived Benzyl and Alkyl 1,2,3-Triazoles as Potential Antifungal and Antibacterial Agents
作者:Jin-Jian Wei、Lei Jin、Kun Wan、Cheng-He Zhou
DOI:10.5012/bkcs.2011.32.1.229
日期:2011.1.20
A series of novel glucose derived benzyl and alkyl 1,2,3-triazoles and their hydrochlorides have been synthesized via Cu(I)-catalyzed 1,3-dipolar cycloaddition. All the new compounds were characterized by MS, IR and NMR spectra. The DEPT, APT, $^1H$-$^1H$ and $^1H-^13}C$ 2D NMR spectra for some compounds were also recorded. These compounds were evaluated for their in vitro antibacterial activities against Staphylococcus aureus ATCC 29213, Bacillus subtilis, Bacillus proteus, Pseudomonas aeruginosa, Escherichia coli ATCC 25922, and antifungal activities against Candida albicans and Aspergillus fumigatus. The bioactive data revealed that (3R,4S,5S,6S)-2-(hydroxymethyl)-6-methoxy-4,5-bis((1-octyl-1H-1,2,3-triazol-4-yl)methoxy)-tetrahydro-2H-pyran-3-ol 8a exhibited excellent antifungal activity against A. fumigatus with an MIC value of 0.055 mM compared to Fluconazole. It also showed broad inhibitory efficacy against tested bacterial strains with MIC values ranging from 0.049 mM to 0.39 mM.
通过Cu(I)催化的1,3-偶极环加成反应,合成了一系列新颖的葡萄糖衍生的苄基和烷基1,2,3-三唑及其盐酸盐。所有新化合物均通过MS、IR和NMR光谱进行了表征。对部分化合物还记录了DEPT、APT、$^1H$-$^1H$和$^1H-^13}C$二维NMR光谱。这些化合物在体外对金黄色葡萄球菌ATCC 29213、枯草芽孢杆菌、变形杆菌、铜绿假单胞菌、大肠杆菌ATCC 25922进行了抗菌活性评估,并对白色念珠菌和烟曲霉进行了抗真菌活性评估。生物活性数据显示,(3R,4S,5S,6S)-2-(羟甲基)-6-甲氧基-4,5-双((1-辛基-1H-1,2,3-三唑-4-基)甲氧基)-四氢-2H-吡喃-3-醇8a对烟曲霉表现出优异的抗真菌活性,MIC值为0.055 mM,相比于氟康唑。它还对测试的细菌菌株显示出广泛的抑制效果,MIC值范围从0.049 mM到0.39 mM。