【作者】 张璇；

【导师】 祖元刚；

【作者基本信息】 东北林业大学 ， 生药学， 2011， 硕士

【摘要】 苯并咪唑是一种重要的医药中间体,特殊的结构使它具有广泛而重要的生理活性,因此合成具有苯并咪唑结构的化合物对新药开发和生物化学研究有着非常重要的意义。本文在苯并咪唑的合成工艺中做了许多大胆而又有意义的尝试和探索,确立了以N-乙基吡啶四氟硼酸盐离子液体作为催化剂微波辅助合成苯并咪唑的绿色合成方法,得到了一系列苯并咪唑衍生物,并进行了结构鉴定和初步体外抗菌活性研究,结果如下：1、确立了苯并咪唑的绿色合成方法：催化剂为N-乙基吡啶四氟硼酸盐离子液体,反应溶剂为无水乙醇,邻苯二胺与醛及催化剂的摩尔比为1：1：0.2,反应温度25℃,微波功率为500 W,微波反应时间2 h,将反应液倒入一定量的冰水混合物中,得粗产物,然后重结晶,采用本方法合成的2-苯基苯并咪唑的收率为90.8%,其结构经IR、1HNMR及MS确定。2、以N-乙基吡啶四氟硼酸盐离子液体作为催化剂,微波辅助合成了12种苯并咪唑衍生物。在苯并咪唑衍生物的合成的过程中,以苯并咪唑的绿色合成方法为手段,将绿色化学应用到苯并咪唑衍生物的合成中来,得到的苯并咪唑衍生物通过IR、1HNMR、MS手段进行鉴定。3、确定了12个苯并咪唑衍生物的初步体外抗菌效果。结果表明,苯并咪唑衍生物B10-B12化合物对革兰氏阳性菌和革兰氏阴性菌都有明显抑菌作用,其中敏感菌株为金黄色葡萄球菌、表皮葡萄球菌、大肠杆菌和绿脓杆菌,其MIC值为1 mg/mL,对大肠杆菌MBC值为4 mg/mL,对金黄色葡萄球菌、表皮葡萄球菌、大肠杆菌和绿脓杆菌抑菌直径大于1.5mm。更多还原

【Abstract】 Benzimidazole was important intermediated products which had been used in medicine, it had extensive and important activities due to special structure, so it is very important to synthesize a series of new benzoimidazoles in new drug development and biochemistry research. In this paper, so many innovative methods were used in benzimidazole technology synthesis, a series of new benzimidazole compounds were synthesized by the reaction under microwave irradiation using ionic liquid [Etpy] BF4 as the catalyst then confirmed structure by 1H NMR, IR or MS and study the antimicrobial activities.1. The green condition of the synthesis of benzoimidazole:Ionic liquid [Etpy]BF4 was used as the catalyst, alcohol was used as solvents, M(o-phenylenediamine):M(aldehyde): M([Etpy]BF4)= 1:1:0.2, microwave power of 500 W and irradiation time of 2 h under 25℃, put the reaction solution into an amount of ice water to get crude product, and then recrystallized, the conversion rate was 90.8%. The synthesized compound was characterized and confirmed by IR、1H NMR and MS.2. Twelve benzimidazole compounds were synthesized by [Etpy] BF4 under microwave irradiation according to the green condition, the structures of twelve benzimidazole compounds were confirmed by 1H NMR, IR or MS.3. The preliminary antibacterial activity of twelve benzimidazole compounds were studied. Results showed that B10-B12 compounds showed greatest antimicrobial toward both gram-positive and gram-negative bacteria, the most sensitive stains were Staphylococcus aureus, Staphylococcus epidermidis, Escherichia coli and Pseudomonas Aeruginosa with MIC value of 1 mg/mL, MBC value of Escherichia coli were 4 mg/mL, inhibition zone of Staphylococcus aureus, Staphylococcus epidermidis, Escherichia coli and Pseudomonas Aeruginosa were above 1.5 mm.更多还原