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Vol. 26 No. 2 (2014): Vol 26 Issue 2

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Synthesis, Characterization and Antimicrobial Activity of Three Gallates Containing Imidazole, Benzimidazole and Triclosan Units

https://doi.org/10.14233/ajchem.2014.15600
Zhiyuan Wang1
1Key Laboratory of Leather Chemistry and Engineering of Ministry of Education, Sichuan University, Chengdu 610065, P.R. China 2National Engineering Laboratory for Clean Technology of Leather Manufacture, Sichuan University, Chengdu 610065, P.R. China *Corresponding author: Fax: +86 28 85405237; Tel: +86 28 85404462; E-mail: guhaibing@scu.edu.cn
Haibin Gu1
1Key Laboratory of Leather Chemistry and Engineering of Ministry of Education, Sichuan University, Chengdu 610065, P.R. China 2National Engineering Laboratory for Clean Technology of Leather Manufacture, Sichuan University, Chengdu 610065, P.R. China *Corresponding author: Fax: +86 28 85405237; Tel: +86 28 85404462; E-mail: guhaibing@scu.edu.cn
Wuyong Chen1
1Key Laboratory of Leather Chemistry and Engineering of Ministry of Education, Sichuan University, Chengdu 610065, P.R. China 2National Engineering Laboratory for Clean Technology of Leather Manufacture, Sichuan University, Chengdu 610065, P.R. China *Corresponding author: Fax: +86 28 85405237; Tel: +86 28 85404462; E-mail: guhaibing@scu.edu.cn

Asian Journal of Chemistry, Vol. 26 No. 2 (2014): Vol 26 Issue 2

Abstract

Three new gallates containing the antimicrobial units of imidazole, benzimidazole and triclosan, respectively, were designed and synthesized. Firstly, the direct esterification method, in which p-toluenesulfonic acid was used as the catalyst, was adopted to synthesize the three gallates. Results show that it is infeasible to obtain the target products, especially for the direct esterification reaction of 5-methyl-2-nitro-imidazole-1-ethanol and gallic acid, the synthesized product is just a complex composed by equimolar 5-methyl-2-nitro-imidazole-1-ethanol and gallic acid and stabilized by a lot of intramolecular and intermolecular hydrogen bonds, which was proved by the single-crystal X-ray diffraction analysis. Another, the indirect esterification method, in which the phenolic hydroxyl groups of gallic acid were first protected by acetyls as shown in Scheme-I, was employed. The obtained compounds were proved to be the expected products by elemental analysis, IR, 1H NMR, 13C NMR and X-ray single-crystal diffraction. Finally, the inhibition zone method was used to determine the antimicrobial effect of the synthesized gallates and their initial compounds. Results indicate that the introduction of the three antimicrobial units has obvious synergistic or additive effect on the antimicrobial activities of gallates. The gallates shows different inhibitory effect against different tested microbes, which is mainly decided by the introduced antimicrobial units.

Keywords

Gallates Imidazole Benzimidazole Triclosan Antimicrobial activity Crystal structure.
Wang1, Z., Gu1, H., & Chen1, W. (2014). Synthesis, Characterization and Antimicrobial Activity of Three Gallates Containing Imidazole, Benzimidazole and Triclosan Units. Asian Journal of Chemistry, 26(2), 513–520. https://doi.org/10.14233/ajchem.2014.15600
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References
  1. C.Y. Bo, L.W. Bi, Z.D. Zhao, Q.G. Zhang, D.M. Li, Y. Gu and J. Wang, Modern Chem. Ind., 28, 393 (2008).
  2. Q. He, K. Yao and B. Shi, China Surfact. Deterg. Cosmet., 30, 29 (2000).
  3. C. Jo, I. Y. Jeong, N. Y. Lee, K. S. Kim and M. W. Byun, Food Sci. Biotechnol., 15, 317 (2006).
  4. C.Y. Bo, L.W. Bi, Z.D. Zhao, D.M. Li, Y. Gu, J. Wang, Q.G. Zhang, Y.M. Wang and Y.H. Zhou, Biomass Chem. Eng., 43, 1 (2009).
  5. J.Q. Zhang and K. Yao, Food Ferment. Technol., 46, 19 (2010).
  6. O.S. Maldonado, R. Lucas, F. Comelles, M.J. González, J.L. Parra, I. Medina and J.C. Morales, Tetrahedron, 67, 7268 (2011); doi:10.1016/j.tet.2011.07.046.
  7. O. Kamiyama, F. Sanae, K. Ikeda, Y. Higashi, Y. Minami, N. Asano and I. Adachi, A. Kato, Food Chem., 122, 1061 (2010); doi:10.1016/j.foodchem.2010.03.075.
  8. I. Kubo, K. Fujita, K. Nihei and A. Nihei, J. Agric. Food Chem., 52, 1072 (2004); doi:10.1021/jf034774l.
  9. W.J. Zhang, D.Y. Xiong and X.M. Liu, Appl. Chem. Ind., 39, 1849 (2010).
  10. A. Ooshiro, M. Kaji, Y. Katoh, H. Kawaide and M. Natsume, J. Pestic. Sci., 36, 240 (2011); doi:10.1584/jpestics.G10-84.
  11. F.L. Hsu, P.S. Chen, H.T. Chang and S.T. Chang, Int. Biodeter. Biodegrad., 63, 543 (2009); doi:10.1016/j.ibiod.2009.02.005.
  12. S.A. Ibrahim, E.D. Wilson, C.W. Seo, A. Shahbazi and M.M. Salameh, 228th National Meeting of the American-Chemical-Society, Philadelphia, Aug 22-26 (2004).
  13. J.H. Chen, Y.M. Wang, D.M. Wu, Z.S. Wu and C.Z. Wang, Chem. Ind. Forest Prod., 25, 6 (2005).
  14. K.X. Wu, M.Y. Li, L. Chen and X. Chen, Fine Chemicals, 15, 9 (1998).
  15. J.H. Kwak, J.K. In, M.S. Lee, J.Y. Yu, Y.P. Yun, J.T. Hong, S.J. Lee, S.Y. Seo, S.K. Ahn, Y.G. Suh, B.Y. Hwang, H. Lee, K.H. Min and J.K. Jung, Bull. Korean Chem. Soc., 30, 2881 (2009); doi:10.5012/bkcs.2009.30.12.2881.
  16. C. Frey, M. Pavani, G. Cordano, S. Munoz, E. Rivera, J. Medina, A. Morello, J.D. Maya and J. Ferreira, Comp. Biochem. Physiol. A Mol. Integr. Physiol., 146, 520 (2007); doi:10.1016/j.cbpa.2006.03.007.
  17. Y. Xu, G.R. Pang, X.F. Lu, Z.J. Chen, S.T. Sun and J.Z. Song, Chin. J. Ophthalmol., 42, 309(2006).
  18. P.C. Leal, A. Mascarello, M. Derita, F. Zuljan, R.J. Nunes, S. Zacchino and R.A. Yunes, Bioorg. Med. Chem. Lett., 19, 1793 (2009); doi:10.1016/j.bmcl.2009.01.061.
  19. W.M. Soe, M. Giridharan, R.T.P. Lin, M.K. Sakharkar and K.R. Sakharkar, Lett. Drug Des. Discov., 7, 160 (2010); doi:10.2174/157018010790596687.
  20. H. Shibata, T. Nakano, M.A.K. Parvez, Y. Furukawa, A. Tomoishi, S. Niimi, N. Arakaki and T. Higuti, Antimicrob. Agents Chemother., 53, 2218 (2009); doi:10.1128/AAC.00829-08.
  21. X.Y. Lu and W.W. Chen, Acta Pharm. Sinica, 22, 586 (1987).
  22. Z.P. Xiao, R.Q. Fang, L. Shi, H. Ding, C. Xu and H.L. Zhu, Can. J. Chem., 85, 951 (2007); doi:10.1139/v07-107.
  23. E. Nomura, A. Hosoda, H. Morishita, A. Murakami, K. Koshimizu, H. Ohigashi and H. Taniguchi, Bioorg. Med. Chem., 10, 1069 (2002); doi:10.1016/S0968-0896(01)00361-3.
  24. H.B. Gu and W.Y. Chen, China Leather, 34, 12 (2005).
  25. W.Y. Chen and G.Y. Li, Tanning Chemistry, Beijing: China Light Industry Press (2004).
  26. M. Wang and Y.B. Zhang, Modern Agrochemicals, 2, 36 (2003).
  27. Y. Zhang, S. Yang, B.A. Song and D.Y. Hu, Agrochemicals, 47, 164 (2008).
  28. Y.B. Chen, Y.S. Ouyang and X.M. Huang, Industrial Bactericides, Chemical Industry Press, Beijing (2001).
  29. W. X. Zhao, J. Shangqiu Teachers College, 18, 76 (2002).
  30. S.S. Ma, S. Jiang, X.X. Shao, W. Chen and B.Q. Yang, J. Northwest Univ. (Nat. Sci. Ed.), 40, 821 (2010).
  31. CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39).
  32. G. M. Sheldrick, SHELXS97 and SHELXL97. University of Göttingen, Germany (1997).
  33. H.B. Gu, Y. Li, W.Y. Chen and C.Q. Zhao, Leather Sci. Eng., 15, 7 (2005).
  34. C.Q. Zhao, H.B. Gu, Y. Cao, R.Q. Zhou, J. Huang and W.Y. Chen, J. Soc. Leather Technol. Chem., 93, 197 (2009).
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