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Synthesis, Molecular Docking and Biological Evaluation of Napthyl N-Acyl Hydrazone Derivatives
Corresponding Author(s) : G. Rajitha
Asian Journal of Chemistry,
Vol. 34 No. 7 (2022): Vol 34 Issue 7, 2022
Abstract
A series of 2-(benzamido)-N′-((naphthalen-1-yl)methylene)-3-(substituted phenyl)acrylo hydrazides (4a-m, 5a-b) were synthesized by condensation of 2-(benzamido)-3-(substituted phenyl)acrylohydrazides with 1-naphthaldehyde in presence of few drops of acetic acid in ethanol. Structural elucidation of final compounds was confirmed by spectral data. Title compounds were evaluated for antioxidant and antibacterial activities and subjected to in silico studies and molecular docking studies with cyclooxygenase-II (COX-II, PDB I’d: 3LN1) and active compounds from docking studies were selected for in vivo evaluation of their antiinflammatory activity. Among the series, compound 4i showed good antioxidant activity; 5b showed good antibacterial activity. All the six derivatives with good docking scores were selected for in vivo evaluation of their antiinflammatory activity. Among the selected active compounds from docking studies, compound 4m showed good antiinflammatory activity which is comparable with that of standard drug diclofenac. In silico studies indicated that all the compounds followed Lipinski’s rule and exhibited good oral absorption and bioavailability.
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E.J. Corey and D. Enders, Tetrahedron Lett., 17, 3 (1976); https://doi.org/10.1016/S0040-4039(00)71307-4
C. Fraga and E. Barreiro, Curr. Med. Chem., 13, 167 (2006); https://doi.org/10.2174/092986706775197881
A.G. Silva, G. Zapata-Sudo, A.E. Kummerle, C.A.M. Fraga, E.J. Barreiro and R.T. Sudo, Bioorg. Med. Chem., 13, 3431 (2005); https://doi.org/10.1016/j.bmc.2005.03.003
D.S. Cukierman, A.B. Pinheiro, S.L.P. Castiñeiras-Filho, A.S.P. da Silva, M.C. Miotto, A. De Falco, T. de P. Ribeiro, S. Maisonette, A.L.M.C. da Cunha, R.A. Hauser-Davis, J. Landeira-Fernandez, R.Q. Aucélio, T.F. Outeiro, M.D. Pereira, C.O. Fernández and N.A. Rey, J. Inorg. Biochem., 170, 160 (2017); https://doi.org/10.1016/j.jinorgbio.2017.02.020
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M. Shekarchi, L. Navidpour, A.R. Khorami, M. Shekarchi, A. Partoazar, H. Shafaroodi, N. Rahmanipour, A. Shafiee and M. Shekarchi, Iran. J. Pharm. Res., 10, 369 (2011); https://doi.org/10.22037/IJPR.2011.968
S. Thota, D.A. Rodrigues, P.S.M. Pinheiro, L.M. Lima, C.A.M. Fraga and E.J. Barreiro, Bioorg. Med. Chem. Lett., 28, 2797 (2018); https://doi.org/10.1016/j.bmcl.2018.07.015
M.M. Alam, G. Verma, M. Shaquiquzzaman, A. Marella, M. Akhtar and M.R. Ali, J. Pharm. Bioallied Sci., 6, 69 (2014); https://doi.org/10.4103/0975-7406.129170
W.Y. Liu, H.Y. Li, B.X. Zhao, D.S. Shin, S. Lian and J.Y. Miao, Carbohydr. Res., 344, 1270 (2009); https://doi.org/10.1016/j.carres.2009.05.017
M.A. Malik, S.A. Al-Thabaiti and M.A. Malik, Int. J. Mol. Sci., 13, 10880 (2012); https://doi.org/10.3390/ijms130910880
Y.K.C. Silva, C.V. Augusto, M.L.C. Barbosa, G.M.A. Melo, A.C. Queiroz, T.L.M.F. Dias, W.B. Júnior, E.J. Barreiro, L.M. Lima and M.S. Alexandre-Moreira, Bioorg. Med. Chem., 18, 5007 (2010); https://doi.org/10.1016/j.bmc.2010.06.002
G. Rajitha, N. Saideepa and P. Praneetha, Indian J. Chem., 50B, 729 (2011).
M.S. Blois, Nature, 181, 1199 (1958); https://doi.org/10.1038/1811199a0
L. Marcocci, L. Packer, M.-T. Droy-Lefaix, A. Sekaki and M. GardèsAlbert, Methods Enzymol., 234, 462 (1994);
https://doi.org/10.1016/0076-6879(94)34117-6
C. Sowjanya, V. Rama Bharathi, G. Kalpana Devi and G. Rajitha, J. Chem. Pharm. Res., 3, 212 (2011).
C.A. Winter, E.A. Risley and G.W. Nuss, Proc. Soc. Exp. Biol. Med., 111, 544 (1962); https://doi.org/10.3181/00379727-111-27849
O. Ursu, A. Rayan, A. Goldblum and T.I. Oprea, WIREs Comput. Mol. Sci., 1, 760 (2011); https://doi.org/10.1002/wcms.52
M.A. Brito, Braz. J. Pharm. Sci., 47, 797 (2011); https://doi.org/10.1590/S1984-82502011000400017
M. Ayati, Falahati, H. Irannejad and S. Emami, Daru, 20, 1 (2012); https://doi.org/10.1186/2008-2231-20-46
M.J. Ahsan, J.G. Samy, H. Khalilullah, M.S. Nomani, P. Saraswat, R. Gaur and A. Sing, Bioorg. Med. Chem. Lett., 21, 7246 (2011); https://doi.org/10.1016/j.bmcl.2011.10.057
V. Pogaku, K. Gangarapu, S. Basavoju, K.K. Tatapudi and S.B. Katragadda, Bioorg. Chem., 93, 103307 (2019); https://doi.org/10.1016/j.bioorg.2019.103307
H.S. Kareem, A. Ariffin, N. Nordin, T. Heidelberg, A. Abdul-Aziz, K.W. Kong and W.A. Yehye, Eur. J. Med. Chem., 103, 497 (2015); https://doi.org/10.1016/j.ejmech.2015.09.016
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