含水杨醛席夫碱结构的黄酮衍生物的固相合成与抗氧化及抗菌活性

doi:10.11944/j.issn.1000-0518.2015.09.150032

摘要/Abstract

摘要：

7-溴乙氧基黄酮与水杨醛固相反应得到7-邻甲醛基苯氧乙氧基黄酮,该化合物分别与N⁴-取代苯氨基脲类、N⁴-取代氨基硫脲类及取代苯亚氨基乙酰肼类化合物固相研磨反应得到3种类型共14个含水杨醛席夫碱结构的黄酮衍生物。用红外(IR)、核磁共振氢谱(¹H NMR)、质谱(ESI-MS)及元素分析(EA)或高分辨质谱(HR-MS)等技术手段对化合物的结构进行了确证。比较测定了这些新化合物清除超氧自由基(O2-·)、羟自由基(·OH)和2,2-二苯基-1-苦味酰基自由基(DPPH·)的活性及总还原能力,并对化合物进行了抗菌活性测定,结果表明,在0.5 g/L浓度时,多数化合物具有抗氧化活性,表现出较好的抑菌活性,其中尤以化合物3b表现出与氯霉素相当的抗菌活性。

关键词: 水杨醛席夫碱, 黄酮, 固相合成, 抗氧化, 抗菌

Abstract:

The 7-o-formylphenoxy ethoxy flavone was obtained from salicylaldehyde and 7-bromoethoxy flavones by solid phase synthetic method. Then fourteen flavone derivatives containing salicylidene Schiff bases were synthesized by the solid phase condensation reaction of 7-salicylidene ethoxy flavone with substituted N⁴-substituted semicarbazides, N⁴-substituted thiosemicarbazides and N-phenylglycine hydrazides. These new compounds were characterized by IR, ¹H NMR, ESI-MS and EA or HR-MS. Their scavenging effects on the superoxide radical(O2-·), hydroxyl radical(·OH) and DPPH· radical and their total reduction activities as well as the antimicrobial activities in vitro were evaluated. At 0.5 g/L concentration, most of the title compounds exhibit antioxidation effects and relatively antibacterial activity. Among them, the antibacterial activity of compound 3b is comparable to that of the control drug chloramphenicol.

Key words: salicylidene schiff bases, flavone, solid phase synthesis, antioxidation, antibacterial

段志芳,邵玲. 含水杨醛席夫碱结构的黄酮衍生物的固相合成与抗氧化及抗菌活性[J]. 应用化学, 2015, 32(9): 1005-1013.

DUAN Zhifang,SHAO Ling. Solid Phase Synthesis and Biological Activity of Flavone Derivatives Containing Salicylidene Schiff Bases[J]. Chinese Journal of Applied Chemistry, 2015, 32(9): 1005-1013.

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