高等学校化学学报
高等學校化學學報
고등학교화학학보
CHEMICAL JOURNAL OF CHINESE UNIVERSITIES
2015年
1期
102-109
,共8页
三唑%黄酮%抗氧化%抗菌
三唑%黃酮%抗氧化%抗菌
삼서%황동%항양화%항균
Triazole%Flavone%Antioxidation%Antibacterial
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(1 H 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/mL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.
7-羥基黃酮與過量1,2-二溴乙烷反應得到7-溴乙氧基黃酮,將其分彆與3-取代-4-氨基-1,2,4-三唑-5-硫酮肉桂醛席伕堿、3-取代-4-苯基-5-巰基-1,2,4-三唑、3-(α-萘亞甲基)-5-巰基-1,2,4-三唑及3-巰基-5-氨基-1,2,4-三唑肉桂醛席伕堿反應,得到4類共16箇7-三唑硫乙氧基黃酮類衍生物.採用紅外光譜( IR)、覈磁共振氫譜(1 H NMR)、質譜( MS)及元素分析( EA)等方法對化閤物的結構進行瞭確證.測定瞭目標化閤物清除超氧自由基(O-·2)、羥自由基(·OH)和2,2-二苯基-1-苦味酰基自由基(DPPH·)的活性及總還原能力,併測定瞭其抗菌活性.結果錶明,多數化閤物在0.5 mg/mL濃度時具有抗DPPH·活性,其中7-(5-苯亞甲基-4-苯基烯丙亞胺基-1,2,4-三唑-3-硫乙氧基)黃酮(1i)活性較彊；多數化閤物錶現瞭較好的抑菌活性,其中7-(5-苯亞甲基-4-苯基-1,2,4-三唑-3-硫乙氧基)黃酮(2c)對大腸桿菌、金黃色葡萄毬菌和黑麯黴均具有較彊的抑製作用.
7-간기황동여과량1,2-이추을완반응득도7-추을양기황동,장기분별여3-취대-4-안기-1,2,4-삼서-5-류동육계철석부감、3-취대-4-분기-5-구기-1,2,4-삼서、3-(α-내아갑기)-5-구기-1,2,4-삼서급3-구기-5-안기-1,2,4-삼서육계철석부감반응,득도4류공16개7-삼서류을양기황동류연생물.채용홍외광보( IR)、핵자공진경보(1 H NMR)、질보( MS)급원소분석( EA)등방법대화합물적결구진행료학증.측정료목표화합물청제초양자유기(O-·2)、간자유기(·OH)화2,2-이분기-1-고미선기자유기(DPPH·)적활성급총환원능력,병측정료기항균활성.결과표명,다수화합물재0.5 mg/mL농도시구유항DPPH·활성,기중7-(5-분아갑기-4-분기희병아알기-1,2,4-삼서-3-류을양기)황동(1i)활성교강；다수화합물표현료교호적억균활성,기중7-(5-분아갑기-4-분기-1,2,4-삼서-3-류을양기)황동(2c)대대장간균、금황색포도구균화흑곡매균구유교강적억제작용.
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 synthe- sized 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-pheny- lallylideneamino-1,2,4-triazol-5-thiones, 3-substituted-4-phenyl-5-mercapto-1,2,4-triazoles, 3-(α-naphthyl- methene)-5-mercapto-1,2,4-triazole and 3-mercapto-5-phenylallylideneamino-1,2,4-triazole. These new com- pounds were characterized via IR, 1 H NMR, MS and elementary analysis. Their scavenging effects on the superoxide radical( O-·2 ) , 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 concentra- tion 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.
