Abstract
A number of novel 13-membered chalcone-imidazole derivatives were prepared and have been synthesized and characterized by IR, 1H NMR, 13C NMR and elemental analysis, the results conformed well to expected structures. Substituted acetophenones and benzaldehydes were condensed using the Claisen–Schmidt base-catalyzed aldol condensation. Methyl on the aromatic ring of chalcones was brominated by NBS, and then the resulting mixture was reacted with imidazole to get the target compound. Several chalcones showed in vitro antibacterial activity against Gram-bacterial. The results showed that these are potential antibacterial compounds.
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References
A.J.K. Atia, Molecules 14, 2431 (2009)
S. Khabnadideh, Z. Rezaei, A.N. Khalafi, E. Eskandari, Daru 15, 17 (2007)
E.J. Foster, C. Lavigueur, Y.C. Ke, V.E. Williams, J. Mater. Chem. 37, 4062 (2005)
L. Brunsveld, H. Zong, M.E.W. Glasbeek, E.W.J. Meijer, Am. Chem. Soc. 122, 6175 (2000)
H.S. Sang, N.T. Gregory, J.Y.J. Chang, Soft Mater. 2, 889 (2006)
H.T. Nguyen, C. Destrade, J. Malthete, J. Adv. Mater. 9, 375 (1997)
K. Borisch, S. Diele, P. Goring, H. Kresse, C. Tschierske, J. Mater. Chem. 8, 529 (1998)
A.H. Sharba, R.I. Al-Bayati, M. Aouad, N. Rezki, Molecules 10, 1153 (2005)
M. Satyanarayana, P. Tiwari, B.K. Tripathi, A.K. Sriwastava, R. Pratap, Bioorg. Med. Chem. 12, 883 (2004)
S. Mukherjee, N. Kumar, A.K. Parasad, H.G. Raj, M.E. Bracke, C.E. Olsen, S.C. Jain, V.S. Parmar, Bioorg. Med. Chem. 9, 337 (2001)
H.K. Hsieh, L.T. Tsao, J.P. Wang, C.N. Lin, J. Pharm. Pharmacol. 52, 163 (2000)
V.J. Ram, A.S. Saxena, S. Srivastava, S. Chandra, Bioorg. Med. Chem. Lett. 10, 2159 (2000)
L. Zhai, M. Chen, J. Blam, T.G. Theander, S.B. Chiristensen, A. Kharazmi, J. Antimicrob. Chemother. 43, 793 (1999)
R.J. Anto, K. Sukumuran, G. Kuttan, M.N.A. Rao, V. Subbaraju, R. Kuttan, Cancer Lett. 97, 33 (1995)
S.K. Kumar, E. Hager, P. Catherine, H. Gurulingappa, N.E. Davidson, S.R. Khan, J. Med. Chem. 46, 2813 (2003)
S.J. Ji, Z.L. Shen, D.G. Gu, S.Y. Wang, J. Organomet. Chem. 689, 1843 (2004)
M. Prokesova, E. Solcaniova, S. Toma, K.W. Muir, A.A. Torabi, G. Knox, J. Org. Chem. 61, 3392 (1996)
A.G. Nagy, P. Sohar, J. Marton, J. Organomet. Chem. 410, 357 (1991)
A.G. Nagy, J. Organomet. Chem. 291, 335 (1985)
A.G. Nagy, S. Toma, J. Organomet. Chem. 266, 257 (1984)
A.N. Nesmeyanov, G.B. Shulp’in, L.V. Rybin, N.T. Gubenko, M.I. Rybinskaya, P.V. Petrovkii, V.I. Robas, J. Gen. Chem. 44, 1994 (1994)
J. Lu, W.Y. Chen, Chem. Res. Appl. 15, 265 (2003)
P. Boeck, C.A.B. Falcao, P.C. Leal, Bioorganic Med. Chem. 14, 1538 (2006)
W.L.F. Armarego, C.L.L. Chai, Purification of Laboratory Chemicals, 5th edn. (Butterworth-Heinemann, London, 2003)
S. Stankovianski, A. Beno, S. Toma, E. Gono, Chemistry 24, 19 (1970)
F.X. Zhu, J.F. Zhou, H.Q. Xiao, Y.L. Zhu, Chem. Reag. 29, 434 (2007)
D. Villemin, B. Martin, M. Puciova, S. Toma, J. Organomet. Chem. 484, 27 (1994)
S.J. Ji, Z.L. Shen, S.Y. Wang, Chin. Chem. Lett. 14, 663 (2003)
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We are grateful to the Microbiology Institute of the Fourth Military Medical University of China for providing the experiment strains.
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Liu, YT., Sun, XM., Yin, DW. et al. Syntheses and biological activity of chalcones-imidazole derivatives. Res Chem Intermed 39, 1037–1048 (2013). https://doi.org/10.1007/s11164-012-0665-z
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DOI: https://doi.org/10.1007/s11164-012-0665-z