姜黄素-N-取代吡唑类衍生物合成及抑菌活性

为了寻求杀菌剂的新的先导化合物,用姜黄素与取代酰肼反应得到13个新的姜黄素-N-取代吡唑类衍生物,其结构经IR,1H NMR,13C NMR,MS和元素分析所表征,初步抑菌实验结果表明,在1×10-4mol/L浓度下,所有衍生物与姜黄素对比,对枯草杆菌、金黄色葡萄球菌、大肠杆菌、青霉、黑霉有较好的抑菌效果.其中,3,5-二(4-羟基-3-甲氧基苯基乙烯基)-N-脒基吡唑(3c),3,5-二(4-羟基-3-甲氧基苯基乙烯基)-N-(苯并噻唑-2-硫基乙酰基)吡唑(3k),3,5-二(4-羟基-3-甲氧基苯基乙烯基)-N-(香豆素-3-甲酰基)吡唑(3m)有优异的抑菌效果(抑菌圈16.34～23.81 mm).这些结果表明含有噻唑环、脒基、香豆素环取代基可能有助于提高姜黄素-N-取代吡唑类衍生物的活性.

Synthesis and Antibacterial Activities of N-Substituted Pyrazole Curcumin Derivatives

In order to find new lead compounds for the design of new antibacterial drugs,13 novel N-substituted pyrazole curcumin derivatives were synthesized from curcumin and substituted hydrazide.The structures of all new compounds were confirmed by 1H NMR,13C NMR,IR,MS techniques and elemental analysis.The results of their in vitro antibacterial tests indicated that,at the concentration of 1×10-4 mol/L,all of the derivatives displayed better activities than curcumin against B.subtilis,S.aureus,E.coli,A.niger,and Penicillium ch.The compounds 3,5-bis(4-hydroxy-3-methoxystyryl)-1-amidinoparazole(3c),3,5-bis(4-hydroxy-3-methoxystyryl)-1-(banzothiazol-2-sulfenyl)parazole(3k) and 3,5-bis(4-hydroxy-3-methoxystyryl)-1-(coumarin-3-formoryl)parazole(3m) showed remarkable antibacterial activities(with inhibition zone of up 16.34 to 23.81 mm).The results showed that thiazole ring,or guanyl and coumarin ring substituents may enhance the activities of Nsubstituted pyrazole curcumin derivatives.