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Bioactive Formylpyrazole Analogues: Synthesis, Antimicrobial, Antioxidant and Molecular Docking Studies
Corresponding Author(s) : Ajay Kumar Kariyappa
Asian Journal of Chemistry,
Vol. 29 No. 7 (2017): Vol 29 Issue 7
Abstract
A series of six new 3-(1-hydroxynaphthalen-2-yl)-1-aryl-1H-pyrazole-4-carbaldehyde derivatives were synthesized by Vilsmeier-Haack reaction of phenyl hydrazones. The new compounds were characterized by spectral studies and elemental analysis. Synthesized compounds were evaluated in vitro for their antimicrobial and antioxidant susceptibilities. The results suggest that the compounds with methyl and methoxy substitutions in the aromatic ring have good in vitro antimicrobial activities and those with methyl, methoxy and no substitutions possess promising DPPH and hydroxyl free radical scavenging abilities.
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- R.V. Patel, P.K. Patel, P. Kumari, D.P. Rajani and K.H. Chikhalia, Eur. J. Med. Chem., 53, 41 (2012); https://doi.org/10.1016/j.ejmech.2012.03.033.
- J. Boonstra and J.A. Post, Gene, 337, 1 (2004); https://doi.org/10.1016/j.gene.2004.04.032.
- K. Ajay Kumar and M. Govindaraju, Int. J. Chemtech Res., 8, 313 (2015).
- P. Jayaroopa, G. Vasanth Kumar, N. Renuka, M.A. Harish Nayaka and K. Ajay Kumar, Int. J. Pharmtech Res., 5, 264 (2013).
- J. Prabhashankar, V.K. Govindappa and A.K. Kariyappa, Turk. J. Chem., 37, 853 (2013); https://doi.org/10.3906/kim-1209-52.
- C.V.T. Vo and J.W. Bode, J. Org. Chem., 79, 2809 (2014); https://doi.org/10.1021/jo5001252.
- N. Renuka and K. Ajay Kumar, Bioorg. Med. Chem. Lett., 23, 6406 (2013); https://doi.org/10.1016/j.bmcl.2013.09.053.
- A. Hall, A. Billinton, S.H. Brown, N.M. Clayton, A. Chowdhury, G.M.P. Giblin, P. Goldsmith, T.G. Hayhow, D.N. Hurst, I.R. Kilford, A. Naylor, B. Passingham and L. Winyard, Bioorg. Med. Chem. Lett., 18, 3392 (2008); https://doi.org/10.1016/j.bmcl.2008.04.018.
- A.E. Rashad, M.I. Hegab, R.E. Abdel-Megeid, J.A. Micky and F.M. Abdel-Megeid, Bioorg. Med. Chem., 16, 7102 (2008); https://doi.org/10.1016/j.bmc.2008.06.054.
- G. Szabo, J. Fischer, A. Kis-Varga and K. Gyires, J. Med. Chem., 51, 142 (2008); https://doi.org/10.1021/jm070821f.
- A.L.A. Kala, K. Kumara, G. Pavithra, M. Prabhuswamy, K.A. Kumar and N.K. Lokanath, Der Pharma Chemica, 8, 328 (2016).
- M.S. Blois, Nature, 181, 1199 (1958); https://doi.org/10.1038/1811199a0.
- R. Nagamallu, B. Srinivasan, M.B. Ningappa and A.K. Kariyappa, Bioorg. Med. Chem. Lett., 26, 690 (2016); https://doi.org/10.1016/j.bmcl.2015.11.038.
- P. Gurunanjappa and A.K. Kariyappa, Curr. Chem. Lett., 5, 109 (2016); https://doi.org/10.5267/j.ccl.2016.2.002.
- K.R. Raghavendra, N. Renuka, V.H. Kameshwar, B. Srinivasan, K. Ajay Kumar and S. Shashikanth, Bioorg. Med. Chem. Lett., 26, 3621 (2016); https://doi.org/10.1016/j.bmcl.2016.06.005.
- A.-F. Miller, Curr. Opin. Chem. Biol., 8, 162 (2004); https://doi.org/10.1016/j.cbpa.2004.02.011.
- P.J. Hart, M.M. Balbirnie, N.L. Ogihara, A.M. Nersissian, M.S. Weiss, J.S. Valentine and D. Eisenberg, Biochem., 38, 2167 (1999); https://doi.org/10.1021/bi982284u
References
R.V. Patel, P.K. Patel, P. Kumari, D.P. Rajani and K.H. Chikhalia, Eur. J. Med. Chem., 53, 41 (2012); https://doi.org/10.1016/j.ejmech.2012.03.033.
J. Boonstra and J.A. Post, Gene, 337, 1 (2004); https://doi.org/10.1016/j.gene.2004.04.032.
K. Ajay Kumar and M. Govindaraju, Int. J. Chemtech Res., 8, 313 (2015).
P. Jayaroopa, G. Vasanth Kumar, N. Renuka, M.A. Harish Nayaka and K. Ajay Kumar, Int. J. Pharmtech Res., 5, 264 (2013).
J. Prabhashankar, V.K. Govindappa and A.K. Kariyappa, Turk. J. Chem., 37, 853 (2013); https://doi.org/10.3906/kim-1209-52.
C.V.T. Vo and J.W. Bode, J. Org. Chem., 79, 2809 (2014); https://doi.org/10.1021/jo5001252.
N. Renuka and K. Ajay Kumar, Bioorg. Med. Chem. Lett., 23, 6406 (2013); https://doi.org/10.1016/j.bmcl.2013.09.053.
A. Hall, A. Billinton, S.H. Brown, N.M. Clayton, A. Chowdhury, G.M.P. Giblin, P. Goldsmith, T.G. Hayhow, D.N. Hurst, I.R. Kilford, A. Naylor, B. Passingham and L. Winyard, Bioorg. Med. Chem. Lett., 18, 3392 (2008); https://doi.org/10.1016/j.bmcl.2008.04.018.
A.E. Rashad, M.I. Hegab, R.E. Abdel-Megeid, J.A. Micky and F.M. Abdel-Megeid, Bioorg. Med. Chem., 16, 7102 (2008); https://doi.org/10.1016/j.bmc.2008.06.054.
G. Szabo, J. Fischer, A. Kis-Varga and K. Gyires, J. Med. Chem., 51, 142 (2008); https://doi.org/10.1021/jm070821f.
A.L.A. Kala, K. Kumara, G. Pavithra, M. Prabhuswamy, K.A. Kumar and N.K. Lokanath, Der Pharma Chemica, 8, 328 (2016).
M.S. Blois, Nature, 181, 1199 (1958); https://doi.org/10.1038/1811199a0.
R. Nagamallu, B. Srinivasan, M.B. Ningappa and A.K. Kariyappa, Bioorg. Med. Chem. Lett., 26, 690 (2016); https://doi.org/10.1016/j.bmcl.2015.11.038.
P. Gurunanjappa and A.K. Kariyappa, Curr. Chem. Lett., 5, 109 (2016); https://doi.org/10.5267/j.ccl.2016.2.002.
K.R. Raghavendra, N. Renuka, V.H. Kameshwar, B. Srinivasan, K. Ajay Kumar and S. Shashikanth, Bioorg. Med. Chem. Lett., 26, 3621 (2016); https://doi.org/10.1016/j.bmcl.2016.06.005.
A.-F. Miller, Curr. Opin. Chem. Biol., 8, 162 (2004); https://doi.org/10.1016/j.cbpa.2004.02.011.
P.J. Hart, M.M. Balbirnie, N.L. Ogihara, A.M. Nersissian, M.S. Weiss, J.S. Valentine and D. Eisenberg, Biochem., 38, 2167 (1999); https://doi.org/10.1021/bi982284u