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Microwave-Assisted Synthesis of 2-(5-(5-(4-Substituted phenyl)-2-(5-methoxy-2H-chromen-3-yl)-1H-imidazol-1-yl)alkyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione Derivatives and their Antimicrobial Activity
Corresponding Author(s) : D. Ashok
Asian Journal of Chemistry,
Vol. 32 No. 4 (2020): Vol 32 Issue 4, 2020
Abstract
A method for the synthesis of several imidazoles containing isoquinoline scaffolds under conventional and microwave irradiation methods. In the microwave irradiation method gives higher yields with in shorter reaction time as compared to conventional heating method, using green solvents and eco-friendly reaction conditions. All the synthesized derivatives were characterized by IR, NMR and Mass spectral analysis. Furthermore, the title compounds were screened for their in vitro antimicrobial activity against bacteria such as Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Klebsiella pneumonia as well as fungi such as Aspergillus niger, Aspergillus flavus and Fusarium oxysporum. The compounds 8a, 8d, 8e and 8h exhibited better antimicrobial activity against all organisms.
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- G. Aysel, I. Taylan, T. Nalan and O. Gulten, Turkish J. Pharm. Sci., 2, 134 (2005).
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- A. Al-Mulla, Der Pharma Chem., 9, 141 (2017).
- M.F. Brana, M. Cacho, A. Gradillas, B. de Pascual-Teresa and A. Ramos, Curr. Pharm. Des., 7, 1745 (2001); https://doi.org/10.2174/1381612013397113
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- M. Gaba, S. Singh and C. Mohan, Eur. J. Med. Chem., 76, 494 (2014); https://doi.org/10.1016/j.ejmech.2014.01.030
- K.C.S. Achar, K.M. Hosamani and H.R. Seetharamareddy, Eur. J. Med. Chem., 45, 2048 (2010); https://doi.org/10.1016/j.ejmech.2010.01.029
- P. Gupta, S. Hameed and R. Jain, Eur. J. Med. Chem., 39, 805 (2004); https://doi.org/10.1016/j.ejmech.2004.05.005
- F. Hadizadeh, H. Hosseinzadeh, V.S. Motamed Shariaty, M. Seifi and S. Kazemi, Iran. J. Pharm. Res., 7, 29 (2008).
- Y. Ozkay, I. Iskar, Z. Incesu and G. Akalin, Eur. J. Med. Chem., 45, 3320 (2010); https://doi.org/10.1016/j.ejmech.2010.04.015
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References
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B.L. Wilkinson, L.F. Bornaghi, A.D. Wright, T.A. Houston and S.A. Poulsen, Bioorg. Med. Chem. Lett., 17, 1355 (2007); https://doi.org/10.1016/j.bmcl.2006.11.079
S. Joshi and N. Khosla, Bioorg. Med. Chem. Lett., 13, 3747 (2003); https://doi.org/10.1016/j.bmcl.2003.08.017
A. Al-Mulla, Der Pharma Chem., 9, 141 (2017).
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S. Banerjee, E.B. Veale, C.M. Phelan, S.A. Murphy, G.M. Tocci, L.J. Gillespie, D.O. Frimannsson, J.M. Kelly and T. Gunnlaugsson, Chem. Soc. Rev., 42, 1601 (2013); https://doi.org/10.1039/c2cs35467e
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S.M. Sami, R.T. Dorr, A.M. Solyom, D.S. Alberts, B.S.W.A. Iyengar and Remers, J. Med. Chem., 39, 1609 (1996); https://doi.org/10.1021/jm950742g
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X. Qian, Y. Li, Y. Xu, Y. Liu and B. Qu, Bioorg. Med. Chem. Lett., 14, 2665 (2004); https://doi.org/10.1016/j.bmcl.2004.02.059
D. Sharma, B. Narasimhan, P. Kumar, V. Judge, R. Narang, E. De Clercq and J. Balzarini, Eur. J. Med. Chem., 44, 2347 (2009); https://doi.org/10.1016/j.ejmech.2008.08.010
R.V. Shingalapur, K.M. Hosamani and R.S. Keri, Eur. J. Med. Chem., 44, 4244 (2009); https://doi.org/10.1016/j.ejmech.2009.05.021
P.V. Frank, K.S. Girish and B. Kalluraya, J. Chem. Sci., 119, 41 (2007); https://doi.org/10.1007/s12039-007-0007-7
M. Gaba, S. Singh and C. Mohan, Eur. J. Med. Chem., 76, 494 (2014); https://doi.org/10.1016/j.ejmech.2014.01.030
K.C.S. Achar, K.M. Hosamani and H.R. Seetharamareddy, Eur. J. Med. Chem., 45, 2048 (2010); https://doi.org/10.1016/j.ejmech.2010.01.029
P. Gupta, S. Hameed and R. Jain, Eur. J. Med. Chem., 39, 805 (2004); https://doi.org/10.1016/j.ejmech.2004.05.005
F. Hadizadeh, H. Hosseinzadeh, V.S. Motamed Shariaty, M. Seifi and S. Kazemi, Iran. J. Pharm. Res., 7, 29 (2008).
Y. Ozkay, I. Iskar, Z. Incesu and G. Akalin, Eur. J. Med. Chem., 45, 3320 (2010); https://doi.org/10.1016/j.ejmech.2010.04.015
D. Ashok, E.V.L. Madhuri, M. Sarasija, S. Sree Kanth, M. Vijjulatha, M.D. Alaparthi and S.R. Sagurthi, RSC Adv., 7, 25710 (2017); https://doi.org/10.1039/C7RA01550J
R.N. Gedye, F.E. Smith and K.C. Westaway, Can. J. Chem., 66, 17 (1988); https://doi.org/10.1139/v88-003
J. Jacob, Int. J. Chem., 4, 29 (2012) https://doi.org/10.5539/ijc.v4n6p29
G.W. Cardona, A.F. Yepes and R.A. Herrera, Curr. Med. Chem., 25, 3637 (2018); https://doi.org/10.2174/0929867325666180309111428