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This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis, Characterization and in vitro Antimicrobial Screening of Some Novel Series of 2-Azetidinone Derivatives Integrated with Quinoline, Pyrazole and Benzofuran Moieties
Corresponding Author(s) : M. Idrees
Asian Journal of Chemistry,
Vol. 32 No. 4 (2020): Vol 32 Issue 4, 2020
Abstract
A series of 5-(benzofuran-2-yl)-N-(3-chloro-4-(2-(p-tolyloxy) substituted quinolin-3-yl)-2-oxoazetidin-1-yl)-1-phenyl-1H-pyrazole-3-carboxamide derivatives (4a-f) were synthesized with excellent yields by cyclocondensation reaction of 5-(benzofuran-2-yl)-N′-(2-(p-tolyloxy) substituted quinolin-3-yl)methylene)-1-phenyl-1H-pyrazole-3-carbohydrazide (3a-f) with chloroacetyl chloride in presence of triethylamine in DMF. One pot condensation of 5-(benzofuran-2-yl)-1-phenyl-1H-pyrazole-3-carbohydrazide (1) with 2-(p-tolyloxy) substituted quinoline-3-carbaldehyde (2a-f) in ethanol solvent in presence of catalytic amount of acetic acid gave intermediate compounds (3a-f). The structures of newly synthesized compounds have been substantiated through elemental analysis and spectral studies viz. 1H NMR, 13C NMR, IR and mass spectra. All the synthesized compounds were screened for their in vitro antibacterial activity against pathogenic bacteria such as S. aureus and E. coli at different concentrations.
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N.C. Desai and A.M. Dodiya, J. Saudi Chem. Soc., 18, 425 (2014); https://doi.org/10.1016/j.jscs.2011.09.005
S.K. Gawande, S.K. Khadsan, Int. J. Pharm. Sci. Res., 5, 2966 (2014).
A. Deep, P. Kumar, B. Narasimhan, S.M. Lim, K. Ramasamy, R.K. Mishra and V. Mani, Acta Pol. Pharm. Drug Res., 73, 65 (2016).
U. Racha, R. Tammira, M. Pokala, P. Mamidi and A. Tammanaboina, Int. J. Soc. Res. Methodol., 4, 163 (2016).
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B.M. Gurupadayya, M. Gopal, B. Padmashali and Y.N. Manohara, Indian J. Pharm. Sci., 70, 572 (2008); https://doi.org/10.4103/0250-474X.45393
A.K. Verma, R. Kumari, A.K. Singh, R. Maurya and M.C. Sharma, World J. Pharm. Pharm. Sci., 3, 1417 (2014).
K. Ilango and S. Arunkumar, Trop. J. Pharm. Res., 10, 219 (2011); https://doi.org/10.4314/tjpr.v10i2.66567
A. Shaikh and J.S. Meshram, Curr. Bioact. Comp., 14, 134 (2018); https://doi.org/10.2174/1573407213666170201113846
A.I.M. Helmi, M.F. Mahdi and R.F. Al-Smaism, Int. Organ. Sci. Res. J. Pharm. Biol. Sci., 12, 56 (2017).
A. Gupta and A.K. Halve, Open Chem. J., 2, 1 (2006); https://doi.org/10.2174/1874842201502010001
H.N. Nagesh, N. Suresh, G.V.S.B. Prakash, S. Gupta, J.V. Rao and K.V.G.C. Sekhar, Med. Chem. Res., 24, 523 (2015); https://doi.org/10.1007/s00044-014-1142-6
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R.S. Keri and S.A. Patil, Biomed. Pharmacother., 68, 1161 (2014); https://doi.org/10.1016/j.biopha.2014.10.007
A.A. Bekhit, H.M.A. Ashour, Y.S. Abdel-Ghany, A.E.-D.A. Bekhit and A. Baraka, Eur. J. Med. Chem., 43, 456 (2008); https://doi.org/10.1016/j.ejmech.2007.03.030
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W.S. Hamama, A.E. Hassanien, M.G. El-Fedawy and H.H. Zoorob, J. Heterocycl. Chem., 53, 945 (2016); https://doi.org/10.1002/jhet.1747
K. Kaur, M. Jain, R.P. Reddy and R. Jain, Eur. J. Med. Chem., 45, 3245 (2010); https://doi.org/10.1016/j.ejmech.2010.04.011
C. Benard, F. Zouhiri, M. Normand-Bayle, M. Danet, D. Desmaele, H. Leh, J.-F. Mouscadet, G. Mbemba, C.-M. Thomas, S. Bonnenfant, M. Le Bret and J. d’Angelo, Bioorg. Med. Chem. Lett., 14, 2473 (2004); https://doi.org/10.1016/j.bmcl.2004.03.005
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