Synthesis and Antibacterial Activities of N-Substituted Pyrazole Curcumin Derivatives

doi:10.6023/cjoc1202051

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (08): 1487-1492.DOI: 10.6023/cjoc1202051 Previous Articles Next Articles

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姜黄素-N-取代吡唑类衍生物合成及抑菌活性

刘志昌, 王应红, 张元勤, 向清祥

乐山师范学院化学与生命科学学院乐山 614000

收稿日期:2012-02-05 修回日期:2012-03-03 发布日期:2012-04-11
通讯作者: 刘志昌 E-mail:liu_zhichang04@163.com
基金资助:
四川省乐山市科技局重点(No. 08SZD092)和四川省科技厅应用基础(No. 2010JY0148)资助项目.

Synthesis and Antibacterial Activities of N-Substituted Pyrazole Curcumin Derivatives

Liu Zhichang, Wang Yinghong, Zhang Yuanqin, Xiang Qinxiang

College of Chemistry and Life Sciences, Leshan Normal University, Leshan 614000

Received:2012-02-05 Revised:2012-03-03 Published:2012-04-11
Supported by:
Project supported by the Key Foundation of Science and Technology Bureau of Leshan City in Sichuan Province (No. 08SZD092) and the Application of Basic Project of Science and Technology Agency of Sichuan Province (No. 2010JY0148).

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-amidinopara- zole (3c), 3,5-bis(4-hydroxy-3-methoxystyryl)-1-(banzothiazol-2-sulfenyl)parazole (3k) and 3,5-bis(4-hydroxy-3-methoxy- styryl)-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 N- substituted pyrazole curcumin derivatives.

Key words: curcumin, pyrazole, hydrazide, synthesis, antibacterial activity

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Liu Zhichang, Wang Yinghong, Zhang Yuanqin, Xiang Qinxiang. Synthesis and Antibacterial Activities of N-Substituted Pyrazole Curcumin Derivatives[J]. Chin. J. Org. Chem., 2012, 32(08): 1487-1492.

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姜黄素-N-取代吡唑类衍生物合成及抑菌活性

Synthesis and Antibacterial Activities of N-Substituted Pyrazole Curcumin Derivatives

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