7-取代三唑硫乙氧基黄酮衍生物的合成及生物活性

7-羟基黄酮与过量1,2-二溴乙烷反应得到7-溴乙氧基黄酮,将其分别与3-取代-4-氨基-1,2,4-三唑-5-硫酮肉桂醛席夫碱、3-取代-4-苯基-5-巯基-1,2,4-三唑、3-(α-萘亚甲基)-5-巯基-1,2,4-三唑及3-巯基-5-氨基-1,2,4-三唑肉桂醛席夫碱反应,得到4类共16个7-三唑硫乙氧基黄酮类衍生物.采用红外光谱(IR)、核磁共振氢谱(1H NMR)、质谱(MS)及元素分析(EA)等方法对化合物的结构进行了确证.测定了目标化合物清除超氧自由基(O-·2)、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,并测定了其抗菌活性.结果表明,多数化合物在0.5 mg/m L浓度时具有抗DPPH·活性,其中7-(5-苯亚甲基-4-苯基烯丙亚胺基-1,2,4-三唑-3-硫乙氧基)黄酮(1i)活性较强;多数化合物表现了较好的抑菌活性,其中7-(5-苯亚甲基-4-苯基-1,2,4-三唑-3-硫乙氧基)黄酮(2c)对大肠杆菌、金黄色葡萄球菌和黑曲霉均具有较强的抑制作用.

Syntheses and Biological Activities of 7-(Substituted triazolo thioethoxy)flavone Derivatives

Flavone and 1,2,4-triazole derivatives have many different biological activities. According to the active groups combination principle, sixteen 7-(substituted triazolo thioethoxy)flavone derivatives were synthesized by means of the condensation reaction of 7-bromoethoxy flavone, which was synthesized from 7-hydroxy flavone and 1,2-dibromoethane, with four types of 1,2,4-triazole compounds, such as 3-substituted-4-phenylallylideneamino-1,2,4-triazol-5-thiones, 3-substituted-4-phenyl-5-mercapto-1,2,4-triazoles, 3-(α-naphthylmethene)-5-mercapto-1,2,4-triazole and 3-mercapto-5-phenylallylideneamino-1,2,4-triazole. These new compounds were characterized via IR, 1H NMR, MS and elementary analysis. Their scavenging effects on the superoxide radical(O2-·), hydroxyl radical(·OH) and DPPH·radical and their total reduction activities were compared, and the in vitro antimicrobial activities were also tested. The results showed that at the concentration of 0.5 mg/mL, some of the title compounds had scavenging effects on DPPH·, among which 7-(5-phenylmethylene-4-phenylallylideneamino-1,2,4-triazol-3-thioethoxy)flavone(1i) had stronger effect than the others, and the title compound had relatively antibacterial activity, among which 7-(5-phenylmethylene-4-phenyl-1,2,4-triazol-3-thioethoxy)flavone(2c) had stronger effect on E. coli, S. aureus and A. niger than the others.