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2,2'-((1E,1'E)-((1,2,5-恶二唑-3,4-二基)双(氮亚烷基))双(亚甲基))双(4-(苯基二氮烯基)苯酚)的合成、表征、溶剂致变色和生物学性质

Synthesis, characterization, solvatochromism and biological properties of 2,2'-((1E,1'E)-((1,2,5-oxadiazole-3,4-diyl)bis (azanylylidene))bis(methan-ylylidene))bis(4-(phenyldiazenyl)phenol).

作者信息

Kakanejadifard Ali, Azarbani Farideh, Saki Zeinab, Kakanejadifard Sahar, Zabardasti Abedin

机构信息

Department of Chemistry, Faculty of Science, Lorestan University, Khorramabad, Iran.

Department of Biology, Faculty of Science, Lorestan University, Khorramabad, Iran.

出版信息

Spectrochim Acta A Mol Biomol Spectrosc. 2014 Nov 11;132:700-5. doi: 10.1016/j.saa.2014.04.181. Epub 2014 May 10.

DOI:10.1016/j.saa.2014.04.181
PMID:24907973
Abstract

Azo-azomethine dyes 2-((4-amino-1,2,5-oxadiazol-3-ylimino)methyl)-4-(phenyl diazenyl)phenols (2a-h) have been synthesized by condensation reaction of 3,4-diamino-1,2,5-oxadiazole with 2-hydroxy-5-[(E)-(aryldiazenyl)]benzaldehyde (1a-h) in methanol. The structures of dyes have been characterized by elemental analysis, mass, IR, UV-Vis, 1H and 13С NMR spectroscopy. UV-Vis absorption spectra indicated enol-keto tautomeric and positive solvatochromism in compounds 2a-h which is dependent on the substitution, solvent, pH and environment temperature. The synthesized compounds were investigated for their in vitro antioxidant activity by diphenylpicrylhydrazyl assay. Compounds substituted with electron donating groups, such as, alkyl and methoxy groups showed moderate antioxidant activity. The in vitro antibacterial activity of all compounds was determined by disk diffusion method. The test compounds showed varying degree of inhibition against B. cereus and S. aureus strains.

摘要

偶氮-偶氮甲碱染料2-((4-氨基-1,2,5-恶二唑-3-基亚氨基)甲基)-4-(苯基重氮基)苯酚(2a-h)通过3,4-二氨基-1,2,5-恶二唑与2-羟基-5-[(E)-(芳基重氮基)]苯甲醛(1a-h)在甲醇中发生缩合反应合成。染料的结构已通过元素分析、质谱、红外光谱、紫外-可见光谱、1H和13C核磁共振光谱进行了表征。紫外-可见吸收光谱表明化合物2a-h中存在烯醇-酮互变异构现象和正溶剂化显色现象,这取决于取代基、溶剂、pH值和环境温度。通过二苯基苦味酰基肼法研究了合成化合物的体外抗氧化活性。被供电子基团如烷基和甲氧基取代的化合物表现出中等的抗氧化活性。所有化合物的体外抗菌活性通过纸片扩散法测定。测试化合物对蜡状芽孢杆菌和金黄色葡萄球菌菌株表现出不同程度的抑制作用。

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