Abstract
Tetrasubstituted imidazoles were synthesized in high yields via the four-component reaction of aromatic aldehydes, amines, substituted benzils and ammonium acetate catalyzed by a porous CeO2 nanorod. Their anti-cancer activities on the Huh-7 hepatocellular carcinoma cell and antibacterial activities on four bacterial species (wild-type Escherichia coli, wild-type Staphylococcus aureus, Pseudomonas aeruginosa PAM1032 and Escherichia coli-NMD-1) in vitro were evaluated. One compound (5p) was screened out because of its high inhibition rate on all four bacterials at 100 μg/mL. Three products (5p, 5t and 5y) showed a high inhibition rate on the Huh-7 hepatocellular carcinoma cell at 10 μg/mL. The results indicated their potential in new drug development.
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Y. Saima, S. Kharmarui, K.S. Gayen, P. Pandit, D.K. Maiti, Chem. Commun. 48, 6601 (2012)
M. Misono, Chem. Commun. 13, 1141 (2006)
U. Ucucu, N.G. Karaburun, I. Iskdag, II Farmaco. 56, 285 (2001)
J.A. Murry, Curr. Opin. Drug Disc. 6(6), 945 (2003)
H. Veisi, A. Khazaei, L. Heshmati, S. Hemmati, Kor. Chem. Soc. 33(4), 1231 (2012)
I. Yavari, E. Kowsari, Mol. Divers. 13(4), 519 (2009)
H. Konishi, T. Ueda, T. Muto, K. Manabe, Org. Lett. 14, 4722 (2012)
A.P. Kulkarni, C.J. Tonzola, A. Babel, S.A. Jenekhe, Chem. Mater. 16, 4556 (2004)
P. Wu, J.P. Qu, Y.X. Li, X. Guo, D. Tang, X. Meng, R.L. Yan, B.H. Chen, Adv. Synth. Catal. 357(18), 3868 (2015)
H. Debus, Liebigs Ann. Chem. 107(2), 199 (1858)
E. Lunt, C.G. Newton, C. Smith, G.P. Stevens, M.F. Stevens, C.G. Straw, R.J. Walsh, F. Lavelle, J. Med. Chem. 30(2), 357 (1987)
R. C. Elderfield, Heterocyclic compounds. 744 (Wiley, 1957)
Wallach & Schuelze. Ber. 14, 420(1881)
A. Bhatnagar, P.K. Sharma, N. Kumar, Int. J. Phamrm Tech Res. 3(1), 268 (2011)
G. Sharma, Y. Jyothi, P. Lakshmi, Synthetic. Commun. 36(20), 2991 (2006)
M.M. Heravi, F. Derikvand, M. Haghighi, Monatsh. Chem. 139, 31 (2008)
S.D. Sharma, P. Hazarika, D. Konwar, Tetrahedron Lett. 49, 2216 (2008)
S. Balalaie, A. Arabanian, M. Hashtroudi, Monatsh. Chem. 131(9), 945 (2000)
J. Sangshetti, N. Kokare, A. Kotharkar, D. Shinde, Monatsh. Chem. 139(2), 125 (2008)
M.M. Heravi, F. Derikvand, F.F. Bamoharram, J. Mol. Catal. A-Chem. 263, 112 (2007)
A. Mohammed, N. Kokare, J. Sangshetti, D. Shinde, Kor. Chem. Soc. 51(5), 418 (2007)
M. Kidwai, P. Mothsra, V. Bansal, R. Goyal, Monatsh. Chem. 137(9), 1189 (2006)
N.D. Kokare, J.N. Sangshetti, D.B. Shinde, Synthesis 18, 2829 (2007)
H.R. Shaterian, M.J. Ranjbar, J. Mol. Liq. 160, 40 (2011)
A. Davoodnia, M.M. Heravi, Z. Safavi-Rad, N. TavakoliHoseini, Synthetic. Commun. 40, 2588 (2010)
A.R. Karimi, Z. Alimohammadi, J. Azizan, A.A. Mohammadi, R.R. Mohmmadizadeh, Catal. Commun. 7(9), 728 (2006)
L. Nagarapu, S. Apuri, S. Kantevari, J. Mol. Catal. A-Chem. 266, 104 (2007)
S. Kantevari, S.V.N. Vuppalapati, D.O. Birdar, L. Nagarapu, J. Mol. Catal. A-Chem 271, 266 (2007)
J.F. Zhou, Y.Z. Song, Y.L. Zhu, S.J. Tu, Synth. Commun. 35(10), 1369 (2005)
A.R. Karimi, Z. Alimohammadi, M.M. Amini, Mol. Divers. 14, 635 (2010)
R. Hekmat, G. Shoar, F. Rahimzadeh, M. Derikvand, Farzaneh. Synth. Commun. 40, 1270 (2010)
A. Emrani, A. Davoodnia, N.B. Tavakoli-Hoseini, Kor. Chem. Soc. 32, 2385 (2011)
K. Dinesh, D.N. Kommi, A.R. Patel, A.K. Chakraborti, Green Chem. 14, 2038 (2012)
V.P. Reddy, A.V. Kumar, K. Swapna, R.K. Rao, Org. Lett. 11, 1697 (2009)
M.Z. Kassaee, Chem. Lett. 22, 1203 (2011)
S. Santra, A. Majee, A. Hajra, Tetrahedron Lett. 53, 1974 (2012)
M. Kotani, T. Koike, K. Yamaguchi, Green Chem. 8, 735 (2006)
R.L. Oliveria, P.K. Kiyohara, M. Rossi, Green Chem. 12, 144 (2010)
O. Baudoin, M. Cesario, D. Guenard, J. Org. Chem. 67, 1199 (2002)
Y. Zheng, P.D. Stevens, Y. Gao, J. Org. Chem. 71, 537 (2006)
U. Laska, C.G. Frost, J. Price, J. Catal. 268, 318 (2009)
K. Seth, P. Purohit, A.K. Chakraborti, Org. Lett. 16, 2334 (2014)
V. Polshettiwar, B. Baruwati, R.S. Varma, Chem. Commun. 36, 1837 (2009)
V. Polshettiwar, R.S. Varma, Tetrahedron 66, 1091 (2010)
K. Seth, S.R. Roy, A.K. Chakraborti, Chem. Commun. 52, 922 (2016)
R. Abu-Reziq, H. Alper, D. Wang, J. Am. Chem. Soc. 128, 5279 (2006)
C. Che, W. Li, S. Lin, Chem. Commun. 67, 5990 (2009)
S. Shylesh, J. Schweizer, S. Demeshko, Adv. Synth. Catal. 351, 1789 (2009)
K. Seth, S.R. Roy, A. Kumar, A.S. Chakraborti, Catal. Sci. Technol. 6, 2893 (2016)
E. Mohsen, J. Jaber, Z. Maryam, New. J. Chem. doi:10.1039/C5NJ00050E
K.F. Shelke, S.B. Sapkal, S.S. Sonar, B.R. Madje, B.B. Shingate, M.S. Shingate, Bull. Korean Chem. Soc. 30, 1057 (2009)
Acknowledgements
We are grateful to the foundation of the “National Natural Sciences Foundation of China” (No. 21201088, 31300067), “Priority Academic Program Development of Jiangsu Higher Education Institutions”, “Major Project of Natural Science Research of University in Jiangsu” (No. 14KJA430003, 15KJA180002), “Aid project for PhD faculties in Jiangsu Normal University” (13XLR007), and “Science and Technology Planning Project of Xuzhou” (KC15SH080) for financial support.
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Fang, Y., Yuan, R., Ge, Wh. et al. Synthesis and biological evaluation of 1,2,4,5-tetrasubstituted imidazoles. Res Chem Intermed 43, 4413–4421 (2017). https://doi.org/10.1007/s11164-017-2886-7
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DOI: https://doi.org/10.1007/s11164-017-2886-7