姜黄素Mannich碱的合成及抑菌活性
收稿日期: 2014-05-16
修回日期: 2014-06-22
网络出版日期: 2014-07-15
基金资助
四川省乐山市科技局重点(No.08SZD092)、四川省科技厅应用基础(No.2010JY0148)和乐山师范学院(No.Z1321)资助项目.
Synthesis and Antibacterial Activities of Mannich Bases of Curcumin Derivatives
Received date: 2014-05-16
Revised date: 2014-06-22
Online published: 2014-07-15
Supported by
Project supported by the Key Foundation of Science and Technology Bureau of Leshan City in Sichuan Province (No.08SZD092), the Application of Basic Project of Science and Technology Agency of Sichuan Province (No.2010JY0148), and the Project of Leshan Normal University (No.Z1321).
刘志昌 , 王应红 , 曾鸿耀 , 聂万丽 , 向清祥 . 姜黄素Mannich碱的合成及抑菌活性[J]. 有机化学, 2014 , 34(11) : 2345 -2349 . DOI: 10.6023/cjoc201405024
In order to find new lead compounds for the design of new antibacterial drugs, eight novel Mannich bases of the curcumin were synthesized for the first time by Mannich reaction of curcumin, formaldehyde and various secondary amines. All the new synthesized curcumin Mannich base compounds were characterized by 1H NMR, 13C NMR, IR, MS and elemental analysis. These curcumin Mannich bases were tested in vitro against different germ and mildew, and all of them have shown better activities than curcumin against B. subtilis, S. aureus, E. coli, A. niger, and Penicillium ch. The results showed that the curcumin Mannich bases containing piperazine ring have obvious mildew resistance (with inhibition zone of up 16.88 mm to 21.34 mm).
Key words： curcumin; Mannich reaction; Mannich base; synthesis; antimicrobial activity
[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. Exp. Tradit. Med. Formulae 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] ishra, 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] Ireson, 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] Tu, Y. Y.; Xu, X. X.; Qiu, F. Chin. J. Org. Chem. 2012, 32, 852 (in Chinese).(涂永元, 徐先祥, 邱飞, 有机化学, 2012, 32, 852.)
[19] Wei, X. C.; Du, Z. Y.; Tu, Z. Q.; Zhang, K.; Xu, X. T. Chem. Res. Appl. 2010, 22, 527 (in Chinese).(韦星船, 杜志云, 涂增清, 张焜, 徐学涛, 化学研究与应用, 2010, 22, 527.)
[20] Joshi, S.; Khosla, N.; Khare, D.; Sharda, R. Bioorg. Med. Chem. Lett. 2005, 15, 221.
[21] Hall, I. H.; Lee, K.-H.; Mar, E. C.; Starnes, C. O.; Waddell, T. G. J. Med. Chem. 1977, 20, 333.
[22] Gevorgyan, G. A.; Agababyan, A. G.; Mndzhoyan, O. L. Russ. Chem. Rev. 1984, 53, 561.
[23] Xu, Q. G.; Liu, T.; Tian, R.; Ma, D. Y.; Li, Q. Chin. J. Org. Chem. 2008, 28, 234 (in Chinese).(徐启贵, 刘天渝, 田睿, 马德银, 李勤耕, 有机化学, 2008, 28, 234.)
[24] Zhou, Z. W.; Yan, J. F.; Tang, X. M.; Zhang, W. Y.; Zhang, Y. X.; Chen, X.; Su, X. Y.; Yang, D. C. Chin. J. Org. Chem. 2010, 30, 582 (in Chinese).(周祖文, 晏菊芳, 唐雪梅, 张蔚瑜, 张映霞, 陈欣, 苏小燕, 杨大成, 有机化学, 2010, 30, 582.)
[25] Wang, B.; Zhao, L. X.; Ji, Z. Z. Chin. Med. Chem. 2000, 10, 26 (in Chinese). (王飚, 赵临襄, 计志忠, 中国药物化学杂志, 2000, 10, 26.)
[26] Zhang, W, G.; Zhang, Hong. W.; Zheng, Z,; Liu, Bai. L.; Ji, Z. Z. J. Shenyang Pharm. Univ. 2000, 17, 30 (in Chinese).(张为革, 张宏伟, 郑直, 刘百里, 计志忠, 沈阳药科大学学报, 2000, 17, 30.)
[27] Tramontini, M. Synthesis 1973, 703.
[28] Arend, M.; Westermann, B.; Risch. N. Angew. Chem., Int. Ed. 1998, 37, 1044.
[29] Jin, W. H. J. Zhejiang Ocean Univ. (Nat. Sci. Ed.) 2003, 22, 52 (in Chinese).(金卫红, 浙江海洋学院学报(自然科学版), 2003, 22, 52.)
[30] Liu, Z. C.; Wang, Y. H.; Zhang, Y. Q.; Xiang, Q. X. Chin. J. Org. Chem. 2012, 32, 1487 (in Chinese).(刘志昌, 王应红, 张元勤, 向清祥, 有机化学, 2012, 32, 1487.)Li, Y.-L. Clinical Microbiology and Inspection, People’s Health Press, Beijing, 1995, p. 77 (in Chinese).(李影林, 临床微生物学及检验, 人民卫生出版社, 北京, 1995, p. 77.)
/
| 〈 |
|
〉 |
