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2012 , Vol. 32 >Issue 08: 1487 - 1492

DOI: https://doi.org/10.6023/cjoc1202051

研究论文

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
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  • 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

  网络出版日期: 2012-04-11

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.

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Synthesis and Antibacterial Activities of N-Substituted Pyrazole Curcumin Derivatives

  • Liu Zhichang ,
  • Wang Yinghong ,
  • Zhang Yuanqin ,
  • Xiang Qinxiang
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  • College of Chemistry and Life Sciences, Leshan Normal University, Leshan 614000

Received date: 2012-02-05

  Revised date: 2012-03-03

  Online 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).

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摘要

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1×10-4 mol/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.

关键词： 姜黄素; 吡唑; 酰肼; 合成; 抑菌活性

本文引用格式

刘志昌 , 王应红 , 张元勤 , 向清祥 . 姜黄素-N-取代吡唑类衍生物合成及抑菌活性[J]. 有机化学, 2012 , 32(08) : 1487 -1492 . DOI: 10.6023/cjoc1202051

Abstract

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

参考文献

[1] Rao, T. S.; Basu, N.; Siddiqui, H. H. Indian J. Med. Res. 1982, 75, 574.

[2] Claramunt, R. M.; Bouissane, L.; Cabildo, M. P.; Cornago, M. P. Elguero, J.; Radziwon, A.; Medina, C. Bioorg. Med. Chem. 2009, 17, 1290.

[3] Sun, Y. M.; Zhang, H. Y.; Chen, D. Z.; Liu, C. B. Org. Lett. 2002, 4, 2909.

[4] Masuda, T.; Toi, Y.; Bando, H.; Maekawa, T.; Takeda, Y.; Yamaguchi, H. J. Agric. Food Chem. 2002, 50, 2524.

[5] Selvam, C.; Jachak, S. M.; Thilagavathi, R.; Chakraborti, A. K. Bioorg. Med. Chem. Lett. 2005, 15, 1793.

[6] Zhong, Y. N.; Zhen, H. S.; Teng, J. B.; Meng, B. H. Chin. J. Exper. Trad. Med. Form. 2008, 14, 46 (in Chinese).

(钟益宁, 甄汉深, 滕建北, 孟保华, 中国实验方剂学杂志, 2008, 14, 46.)

[7] Mishra, S.; Narain, U.; Mishra, R.; Misra, K. Bioorg. Med. Chem. 2005, 13, 1477.

[8] Mishra, S.; Karmodoya, K.; Surolia, N., Surolia, A. Bioorg. Med. Chem. 2008, 16, 2894.

[9] Mazumder, A.; Neamati, N.; Sunder, S.; Schulz, J.; Pertz, H.; Eich, E.; Pommier, Y. J. Med. Chem. 1997, 40, 3057.

[10] Mazumder, A.; Raghavan, K.; Weinstein, J.; Kohn, K. W.; Pommier, Y. Biochem. Pharmacol. 1995. 49, 1165.

[11] lreson, C. R.; Jones, D. J. L.; Samantha, O. Cancer Epidemiol. Biomarkers Prev. 2002, 11, 105．

[12] Shim, J. S.; Kim, D. H.; Jung, H. J.; Kim, J. H.; Lim, D.; Lee, S. K.; Kim, K. W.; Ahn, J. W.; Yoo, J. S.; Rho, J. R.; Shin, J.; Kwon, H. J. Bioorg. Med. Chem. 2002, 10, 2987.

[13] Lin, L.; Shi, Q.; Alexander, K; Nyarko, A. K.; Bastow, K. F.; Wu, C. C.; Su, C. Y.; Shih, C. C.-Y; Lee, K. H. J. Med. Chem. 2006, 49, 3963.

[14] Simoni, D.; Rizzi, M.; Rondanin, R.; Baruchello, R.; Marchetti, P.; Invidiata, F. P.; Labbozzetta, M.; Poma, P.; Carina, V.; Notarbartolo, M.; Alaimo, A.; D'Alessandro, N. Bioorg. Med. Chem. Lett. 2008, 18, 845.

[15] Labbozzetta, M.; Baruchello, R.; Marchetti, P.; Gueli, M. C.; Poma, P.; Notarbartolo, M.; Simoni, D.; D'Alessandro, N. Chem.-Biol. Interact. 2009, 181, 29.

[16] Zhou, S. S.; Xue, X.; Jiang, B.; Lu, C. H., Tian, Y. P.; Jiang, M. H. Acta Chim. Sinica 2011, 69, 2335 (in Chinese). (周双生, 薛璇, 姜波, 鲁传华, 田玉鹏, 蒋明华, 化学学报, 2011, 69, 2335.)

[17] Airoldi, C.; Zona, C.; Sironi, E.; Colombo, L.; Messa, M.; Aurilia, D.; Gregori, M.; Masserini, M.; Salmona, M.; Nicotra, F.; Ferla, B. L. J. Biotechnol. 2011, 156, 317.

[18] Gong, X. Q.; Chen, N. C. West China J. Pharm. Sci. 1997, 12, 240 (in Chinese). (龚筱群, 陈洪超, 华西药学杂志, 1997, 12, 240.) Li, Y. L. Clinical Microbiology and Inspection, People’s Health Press, Beijing, 1995, pp. 77～82 (in Chinese). (李影林, 临床微生物学及检验, 人民卫生出版社, 北京, 1995, pp. 77～82.)
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