Abstract
Here we reported the synthesis of N-substituted imidazole derivatives (VIa–o) that involves Suzuki coupling reaction between 1-(2-((4-bromobenzyl)oxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole (V) and various aryl boronic acids using Pd(dppf)Cl2 with DCM as the catalyst in 1,4-dioxane/H2O (2 : 1) solvent and using potassium carbonate as base. All the newly synthesized compounds were characterized by 1H NMR, 13C NMR and mass spectral data. They were screened for their antibacterial activity against gram-positive bacterial strains, Bacillus subtilis and Staphylococcus aureus where the compounds 4-(4-((1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy)methyl)phenyl)pyridine (VIc), 1-(2-(2,4-dichlorophenyl)-2-((3'-fluoro-4'-methoxy-[1,1'-biphenyl]-4-yl)methoxy)ethyl)-1H-imidazole (VIe), 4'-((1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy)methyl)-[1,1'-biphenyl]-3-carbonitrile (VIi), 1-(2-(2,4-dichlorophenyl)-2-((3'-fluoro-[1,1'-biphenyl]-4-yl)methoxy)ethyl)-1H-imidazole (VIj), 1-(2-(2,4-dichlorophenyl)-2-((4'-fluoro-3'-methyl-[1,1'-biphenyl]-4-yl)methoxy)ethyl)-1H-imidazole (VIn) and 4-(4-((1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy)methyl)phenyl)-1H-pyrazole (VIo) exhibited remarkable activity compared to the reference streptomycin.
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REFERENCES
Clardy, J., Fischbach, M.A., and Walsh, C.T., Nat. Biotechnol., 2006, vol. 24, no. 12, pp. 1541–1550. https://doi.org/10.1038/nbt1266
Wright, G., Nature, 2014, vol. 509 (7498), pp. S13–S13. https://doi.org/10.1038/509S13a
Simmons, K.J., Chopra, I., and Fishwick, C.W., Nat. Rev. Microbiol., 2010, vol. 8, no. 7, pp. 501–510. https://doi.org/10.1038/nrmicro2349
Lewis, K., Nat. Rev. Drug. Discov., 2013, vol. 12, no. 5, pp. 371–387. https://doi.org/10.1038/nrd3975
Gaz Serban, A., Boda Francise, A., and Pop Rahela, R., Mini. Rev. Med. Chem., 2021, vol. 21, no. 11, pp. 1380–1392. https://doi.org/10.2174/1389557520999201209213648
Valls, A., Andreu, J.J., Falomir, E., Luis, S.V., Atrián-Blasco, E., Mitchell, S.G., and Altava, B., Pharmaceuticals, 2020, vol. 13, no. 12, p. 482. https://doi.org/10.3390/ph13120482
Mohan, H., Medicinal Chemistry Textbook, 2010, 10th ed., pp. 519−521.
Vijesh, A.M., Isloor, A.M., Telkar, S., Peethambar, S.K., Rai, S., and Isloor, N., Eur. J. Med. Chem., 2011, vol. 46, pp. 3531–3536. https://doi.org/10.1016/j.ejmech.2011.05.005
Padmavathi, V., Kumara, C.P., Venkatesh, B.C., and Padmaja, A., Eur. J. Med. Chem., 2011, vol. 46, no. 11, pp. 5317−5326. https://doi.org/10.1016/j.ejmech.2011.08.032
Ramachandran, R., Rani, M., Senthan, S., Jeong, Y.T., and Kabilan, S., Eur. J. Med. Chem., vol. 46, no. 5, pp. 1926−1934. https://doi.org/10.1016/j.ejmech.2011.02.036
Naaz, F., Srivastava, R., Singh, A., Singh, N., Verma, R., Singh, V.K., and Singh, R.K., Bioorg. Med. Chem., 2018, vol. 26, pp. 3414–3482. https://doi.org/10.1016/j.bmc.2018.05.015
Mallié, M., Bastide, J.M., and Wade, A., Int. J. Antimicrob. Agents, 2005, vol. 25, no. 4, pp. 321–328. https://doi.org/10.1016/j.ijantimicag.2004.11.010
Subramaniam, P. and Nandan, N., Contemp. Clin. Dent., 2011, vol. 2, no. 4, pp. 287–290. https://doi.org/10.4103%2F0976-237X.91790
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Sudheer Reddy, V., Reddy, N.R., Reddy, A.V. et al. Synthesis of Some New N-Substituted Imidazole Derivatives and Their In Vitro Antibacterial Investigation. Russ J Bioorg Chem 48, 643–650 (2022). https://doi.org/10.1134/S1068162022030189
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DOI: https://doi.org/10.1134/S1068162022030189