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Synthesis and Antimicrobial Activities of a Series of 2,5-Substituent 1,4-Cyclohexanedione Derivatives
Corresponding Author(s) : Hui-Lian Liu
Asian Journal of Chemistry,
Vol. 25 No. 3 (2013): Vol 25 Issue 3
Abstract
A series of 2,5-substituent 1,4-cyclohexanedione derivatives compounds were designed and synthesized. Their structures were identified by elemental analysis, 1H NMR, IR spectra. Their assayed antibacterial (Escherichia coli, Bacillus subtilis) and antifungal (Candida albicans) activities were also evaluated by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide) method. The results of biological test showed 2,5-dibenzylformate 1,4-cyclohexanedione (11) and 2,5-diformanilide 1,4-cyclohexanedione (12) have favorable antimicrobial activity with MICs of 26.7, 33.6, 24.2 and 32.3 μg/mL against Escherichia coli and Bacillus subtilis, respectively.
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References
D.T.W. Chu, J.J. Plattner and L. Katz, J. Med. Chem., 39, 3853 (1996).
K.M. Overbye and J.F. Barrett, Drug Discov. Today, 10, 45 (2005).
L. Otvos Jr., J.D. Wade, F. Lin, B.A. Condie, J. Hanrieder and R. Hoffmann, J. Med. Chem., 48, 5349 (2005).
H. Xin and K.A. Reynolds, Antimicrob. Agents Chemother., 46, 1310 (2002).
Y. Cui, Y. Dang, Y. Yang, S. Zhang and R. Ji, Eur. J. Med. Chem., 40, 209 (2005).
A.T. Nielsen, Org. Synth., 45, 25 (1965).
A.J. Fatiad, Synthesis, 65 (1976).
K.J. Boosen, Helv. Chim. Acta, 60, 1256 (1977).
S.X. Wang, M. Mure, K.F. Medzihradsky, A.L. Burlingame, R.A. Brown, D.M. Dooley, A.J. Smith, H.M. Kagan and J.P. Klinman, Science, 273, 1076 (1996).
C. Basavaraja, N.R. Kim, H.T. Park and D.S. Huh, Bull. Korean Chem. Soc., 30, 4907 (2009).
T. Bánsági Jr. and O. Steinbock, Chaos, 18, 026102 (2008).
P. Cao, X.F. Huang, H. Ding, H.M. Ge, H.Q. Li, B.F. Ruan and H.L. Zhu, Chem. Biodivers, 4, 881 (2007).
J. Meletiadis, J.F. Meis, J.W. Mouton, J.P. Donnelly and P.E. Verweij, J. Clin. Microbiol., 38, 949 (2000).