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Molecular Docking Study of Novel Synthesized Pyrazole Derivatives and their Antibacterial Activity
Corresponding Author(s) : M.R. Ezhilarasi
Asian Journal of Chemistry,
Vol. 30 No. 4 (2018): Vol 30 Issue 4
Abstract
The current novel series of 1-[5-(furan-2-yl)-4,5-dihydro-3-(4-morpholinophenyl)pyrazol-1-yl]ethanone are synthesized from the 3-(furan-2-yl)-1-(4-morpholinophenyl)prop-2-ene-1-one by cyclization reaction. The 3-(furan-2-yl)-1-(4-morpholinophenyl)prop-2-ene-1-one chalcones are derived from the reaction of 4-morpholino acetophenone with substituted furfuraldehyde by common Claisen-Schmidt condensation reaction. The structures of the synthesized compounds skeleton are elucidated by IR, 1H NMR and 13C NMR. The antimicrobial susceptibility tests of synthesized compounds are screened against Staphylococcus aureus and Escherichia coli. From the three synthesized compounds the electron-withdrawing substitution (Br) shows good effect against the Gram-positive bacteria and the electron donating substitution (CH3) shows excellent inhibition zone against the Gram-negative bacteria at the concentration level (10 μg/mL). The molecular docking is an effective and component tool for in silico screening of bioactive compounds and Auto Dock 4.2.1 is used to find the binding interaction of synthesized compounds towards 3 selected bacterial proteins (2X5O, 3TYE, 3UDI).
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- V. Kumar, K. Kaur, G.K. Gupta and A.K. Sharma, Eur. J. Med. Chem., 69, 735 (2013); https://doi.org/10.1016/j.ejmech.2013.08.053.
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- R. Aggarwal, V. Kumar and S.P. Singh, Indian J. Chem., 46B, 1332 (2007).
- D.C. Malvar, R.T. Ferreira, R.A. de Castro, L.L. de Castro, A.C.C. Freitas, E.A. Costa, I.F. Florentino, J.C.M. Mafra, G.E.P. de Souza and F.A. Vanderlinde, Life Sci., 95, 81 (2014); https://doi.org/10.1016/j.lfs.2013.12.005.
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- N. Shao, T. Chen, T. Zhang, H. Zhu, Q. Zheng and H. Zou, Tetrahedron, 70, 795 (2014); https://doi.org/10.1016/j.tet.2013.12.046.
- M.R. Ezhilarai and B. Prabha, Res. J. Chem. Sci., 5, 1 (2015).
- R. Surendra Kumar, I.A. Arif, A. Ahamed and A. Idhayadhulla, Saudi J. Biol. Sci., 23, 614 (2016); https://doi.org/10.1016/j.sjbs.2015.07.005.
- K.T. Ashish, M. Anil, H.N. Verma and A. Mishra, Indian J. Chem., 45B, 489 (2006).
- S. Ningaiah, U.K. Bhadraiah, S.D. Doddaramappa, S. Keshavamurthy and C. Javarasetty, Bioorg. Med. Chem., 24, 245 (2014); https://doi.org/10.1016/j.bmcl.2013.11.029.
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- P.O. Patil and S.B. Bari, Asian J. Chem., 25, 3588 (2013); https://doi.org/10.14233/ajchem.2013.13662.
- M.R. Ezhilarasi, B. Prabha and M. Kulandhaivel, Eur. J. Pharm. Med. Res., 2, 355 (2015).
- I. Loewe, W.R. Balzer and S. Gerstung, Chem. Abstr., 128, 16281 (1997).
- I. Çelik, N. Kaniskan and S. Kökten, Tetrahedron, 65, 328 (2009); https://doi.org/10.1016/j.tet.2008.10.047.
- S. Yadav, P. Rai, M. Srivastava, J. Singh, K.P. Tiwari and J. Singh, Tetrahedron Lett., 56, 5831 (2015). https://doi.org/10.1016/j.tetlet.2015.07.039.
- M.R. Ezhilarasi, B. Prabha and T. Santhi, Chem. Sci. Rev. Lett., 4, 1216 (2015).
- V. Kanagarajan, M.R. Ezhilarasi and M. Gopalakrishnan, Spectrochim. Acta A Mol. Biomol. Spectrosc., 78, 635 (2011); https://doi.org/10.1016/j.saa.2010.11.038.
- V. Kanagarajan, M.R. Ezhilarasi and M. Gopalakrishnan, Org. Med. Chem. Lett., 1, 8 (2011); https://doi.org/10.1186/2191-2858-1-8.
- M. Rani and Y. Mohamad, J. Saudi Chem. Soc., 18, 411 (2014); https://doi.org/10.1016/j.jscs.2011.09.002.
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References
V. Kumar, K. Kaur, G.K. Gupta and A.K. Sharma, Eur. J. Med. Chem., 69, 735 (2013); https://doi.org/10.1016/j.ejmech.2013.08.053.
A.M. Vijesh, A.M. Isloor, P. Shetty, S. Sundershan and H.K. Fun, Eur. J. Chem., 62, 410 (2013); https://doi.org/10.1016/j.ejmech.2012.12.057.
R. Aggarwal, V. Kumar and S.P. Singh, Indian J. Chem., 46B, 1332 (2007).
D.C. Malvar, R.T. Ferreira, R.A. de Castro, L.L. de Castro, A.C.C. Freitas, E.A. Costa, I.F. Florentino, J.C.M. Mafra, G.E.P. de Souza and F.A. Vanderlinde, Life Sci., 95, 81 (2014); https://doi.org/10.1016/j.lfs.2013.12.005.
E. Mosaddegh, M.R. Islami and Z. Shojaie, Arab. J. Chem., 10, S1200 (2017); https://doi.org/10.1016/j.arabjc.2013.02.016.
M. Suri, T. Jousseaume, J.J. Neumann and F. Glorius, Green Chem., 14, 2193 (2012); https://doi.org/10.1039/c2gc35476d.
N. Shao, T. Chen, T. Zhang, H. Zhu, Q. Zheng and H. Zou, Tetrahedron, 70, 795 (2014); https://doi.org/10.1016/j.tet.2013.12.046.
M.R. Ezhilarai and B. Prabha, Res. J. Chem. Sci., 5, 1 (2015).
R. Surendra Kumar, I.A. Arif, A. Ahamed and A. Idhayadhulla, Saudi J. Biol. Sci., 23, 614 (2016); https://doi.org/10.1016/j.sjbs.2015.07.005.
K.T. Ashish, M. Anil, H.N. Verma and A. Mishra, Indian J. Chem., 45B, 489 (2006).
S. Ningaiah, U.K. Bhadraiah, S.D. Doddaramappa, S. Keshavamurthy and C. Javarasetty, Bioorg. Med. Chem., 24, 245 (2014); https://doi.org/10.1016/j.bmcl.2013.11.029.
S. Viveka, Dinesha, L.N. Madhu and G.K. Nagaraja, Monatsh. Chem., 146, 1547 (2015); https://doi.org/10.1007/s00706-015-1428-5.
A. Cetin and I. Bildirici, J. Saudi Chem. Soc., (2016); https://doi.org/10.1016/j.jscs.2016.05.008.
M. Shahar Yar, M.A. Bakht, A.A. Siddiqui, M.M. Abdullah and E. De Clercq, J. Enzyme Inhib. Med. Chem., 24, 876 (2009); https://doi.org/10.1080/14756360802447917.
M.D. Altintop, A. Ozdemir, S. Ilgin and O. Atli, Drug Des. Discov., 11, 833 (2014); https://doi.org/10.2174/1570180811666140226235350.
P.B. Miniyar, M.A. Barmade and A.A. Mahajan, J. Saudi Chem. Soc., 19, 655 (2015); https://doi.org/10.1016/j.jscs.2013.12.004.
D. Sriram, P. Yogeeswari, J.S. Basha, D.R. Radha and V. Nagaraja, Bioorg. Med. Chem. Lett., 13, 5774 (2006); https://doi.org/10.1016/j.bmc.2005.05.063.
M. Johnson, B. Younglove, L. Lee, R. Leblanc, H. Holt Jr., P. Hills, H. Mackay, T. Brown, S.L. Mooberry and M. Lee, Bioorg. Med. Chem. Lett., 17, 5897 (2007); https://doi.org/10.1016/j.bmcl.2007.07.105.
P.O. Patil and S.B. Bari, Asian J. Chem., 25, 3588 (2013); https://doi.org/10.14233/ajchem.2013.13662.
M.R. Ezhilarasi, B. Prabha and M. Kulandhaivel, Eur. J. Pharm. Med. Res., 2, 355 (2015).
I. Loewe, W.R. Balzer and S. Gerstung, Chem. Abstr., 128, 16281 (1997).
I. Çelik, N. Kaniskan and S. Kökten, Tetrahedron, 65, 328 (2009); https://doi.org/10.1016/j.tet.2008.10.047.
S. Yadav, P. Rai, M. Srivastava, J. Singh, K.P. Tiwari and J. Singh, Tetrahedron Lett., 56, 5831 (2015). https://doi.org/10.1016/j.tetlet.2015.07.039.
M.R. Ezhilarasi, B. Prabha and T. Santhi, Chem. Sci. Rev. Lett., 4, 1216 (2015).
V. Kanagarajan, M.R. Ezhilarasi and M. Gopalakrishnan, Spectrochim. Acta A Mol. Biomol. Spectrosc., 78, 635 (2011); https://doi.org/10.1016/j.saa.2010.11.038.
V. Kanagarajan, M.R. Ezhilarasi and M. Gopalakrishnan, Org. Med. Chem. Lett., 1, 8 (2011); https://doi.org/10.1186/2191-2858-1-8.
M. Rani and Y. Mohamad, J. Saudi Chem. Soc., 18, 411 (2014); https://doi.org/10.1016/j.jscs.2011.09.002.
C.A. Lipinski, F. Lombardo, B.W. Dominy and P.J. Feeney, Adv. Drug Deliv. Rev., 46, 3 (2001); https://doi.org/10.1016/S0169-409X(00)00129-0.
R. Sri Dharani, R. Ranjitha, R. Sripathi, K.S. Ali Muhammed and S. Ravi, Asian J. Pharm. Clin. Res., 9, 121 (2016); https://doi.org/10.22159/ajpcr.2016.v9i5.12693.