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

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。

Solid Phase Synthesis and Biological Activity of Flavone Derivatives Containing Salicylidene Schiff Bases

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.