1,2,3-三氮唑桥连水杨醛类席夫碱菊糖衍生物的合成及抑菌活性研究 |
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引用本文: | 胡云霞,;李琬聪,;周婷婷,;郭占勇.1,2,3-三氮唑桥连水杨醛类席夫碱菊糖衍生物的合成及抑菌活性研究[J].化学与生物工程,2014(8):27-30. |
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作者姓名: | 胡云霞 ;李琬聪 ;周婷婷 ;郭占勇 |
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作者单位: | [1]中国科学院烟台海岸带研究所海岸带生物学与生物资源利用重点实验室,山东烟台264003; [2]中国科学院大学,北京100049 |
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基金项目: | “十二五”国家科技支撑计划资助项目(2012BAD32B09) |
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摘 要: | 先对菊糖C-6位的羟基进行溴代激活,形成易离去基团,再用叠氮基亲核置换易离去基团,最后将水杨醛类丙炔胺席夫碱中间体通过Huisgen-Click反应与叠氮代菊糖中间体桥连,得到1,2,3-三氮唑桥连水杨醛类席夫碱菊糖衍生物(4a~4c),通过红外光谱对其结构进行了表征,并测定其抑菌活性。结果表明,与菊糖相比,菊糖衍生物的抑菌活性明显提高,当浓度为1 000μg·mL-1时,化合物4a对黄瓜炭疽病菌(Colletotrichum lagenarium)、西瓜枯萎病菌(Fusarium oxysporium)和芦笋茎枯病菌(Phomopsis asparagi)的抑制率分别为66.7%、42.0%和58.1%。通过对菊糖进行针对性化学修饰,接入具有抑菌活性的基团,可以在一定程度上提高菊糖的抑菌活性,为进一步开发利用菊糖提供了依据。
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关 键 词: | 菊糖衍生物 -三氮唑 水杨醛类席夫碱 合成 抑菌活性 |
Synthesis and Antifungal Activity of 1,2,3-Triazole Bridge-Connected Salicylaldehyde Schiff Base Inulin Derivatives |
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Affiliation: | HU Yun-xia, LI Wan-cong, ZHOU Ting-ting, GUO Zhan-yong (1. Key Laboratory of Coastal Biology and Biological Resource Utilization ,Yantai Institute of Coastal Zone Research ,Chinese Academy of Sciences ,Yantai 264003 ,China; 2. University of Chinese Academy of Sciences ,Beijing 100049, China) |
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Abstract: | To get an appropriate leaving group by activating the primary hydroxyl at C-6 position of inulin with the substitution of bromine,which could be displaced conveniently by azide ion through SN reaction,then the salicylaldehyde Schiff base compounds could be easily bridge-connected by Huisgen-Click reaction,the target compouds 1,2,3-triazole bridge-connected salicylaldehyde Schiff base inulin derivatives(4a-4c)were obtained at last.The structures of target compounds were characterized by FTIR,and their antifungal activities were determined.The results showed that the antifungal activities were enhanced remarkably compared to inulin.At the concentration of 1 000μg·mL^-1 ,the inhibition rates of compound 4a against Colletotrichum lagenarium ,Fusarium oxysporium and Phomopsis asparagi were 66.7%,42.0%,58.1%,respectively.The antifungal activity could be improved after grafting some groups with antimicrobial effect via pointed chemical modifica-tion,which provided theory basis for the further utilization of inulin. |
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Keywords: | inulin derivatives 1 2 3-triazole salicylaldehyde Schiff base synthesis antifungal activity |
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