Research Article | Volume: 11, Supplement 1, March, 2021

Design and synthesis of novel 4-aminophenazone Schiff bases by grinding technique as prospective anti-inflammatory agents

Rashmi Arora Rishi Sharma Abhishek Tageza Ajmer Singh Grewal Balraj Saini Sandeep Arora Rajwinder Kaur   

Open Access   

Published:  Feb 08, 2021

DOI: 10.7324/JAPS.2021.11s105
Abstract

Schiff bases are biologically diverse molecules with vast pharmacological activities and have been an area of interest in medicinal chemistry. Recently, this class also attributed new targets for drug development and research. The present study reveals the design and synthesis of the novel Schiff bases as prospective anti-inflammatory agents from the combination of 4-aminopyrazone with different aldehydes with a simple and effective grinding technique to produce different yellow-shaded products. The compounds formed were analyzed by IR spectra and 1H-nuclear magnetic resonance. Synthesized derivatives were evaluated in silico using docking studies to predict phosphodiesterase 7 (PDE7) inhibition and to investigate the binding interactions of the synthesized derivatives with active site residues of PDE7. These compounds showed appreciable binding interactions with PDE7 protein and good drug-like properties.Schiff bases are biologically diverse molecules with vast pharmacological activities and have been an area of interest in medicinal chemistry. Recently, this class also attributed new targets for drug development and research. The present study reveals the design and synthesis of the novel Schiff bases as prospective anti-inflammatory agents from the combination of 4-aminopyrazone with different aldehydes with a simple and effective grinding technique to produce different yellow-shaded products. The compounds formed were analyzed by IR spectra and 1H-nuclear magnetic resonance. Synthesized derivatives were evaluated in silico using docking studies to predict phosphodiesterase 7 (PDE7) inhibition and to investigate the binding interactions of the synthesized derivatives with active site residues of PDE7. These compounds showed appreciable binding interactions with PDE7 protein and good drug-like properties.


Keyword:     4-Aminophenazone antiinflammatory docking PDE7 Schiff bases.


Citation:

Arora R, Sharma R, Tageza A, Grewal AS, Saini B, Arora S, Kaur R. Design and synthesis of novel 4-aminophenazone Schiff bases by grinding technique as prospective anti-inflammatory agents. J Appl Pharm Sci, 2021; 11 (Supp 1):048–053.

Copyright: © The Author(s). This is an open-access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

HTML Full Text

Reference

Aboul-Fadl T, Bin-Jubair FAS. Anti-tubercular activity of isatin derivatives. Int J Res Pharm Sci, 2010; 1(2):113-26.

Akhter S, Zaman HU, Mir S, Dar AM, Shrivastava S. Synthesis of Schiff base metal complexes: a concise review. Eur Chem Bull, 2017; 6(10):475-83. https://doi.org/10.17628/ecb.2017.6.475-483

Alam MS, Choi JH, Lee DU. Synthesis of novel Schiff base analogues of 4-amino-1,5-dimethyl-2-phenylpyrazol-3-one and their evaluation for antioxidant and anti-inflammatory activity. Bioorg Med Chem, 2012; 20:4103-8. https://doi.org/10.1016/j.bmc.2012.04.058

012; 20:4103-8. Al Zoubi W, Al-Hamdani AAS, Kaseem M. Synthesis and antioxidant activities of Schiff bases and their complexes: a review. Appl Organometal Chem, 2016; 30:810-17. https://doi.org/10.1002/aoc.3506

Barnes MJ, Cooper N, Davenport RJ, Dyke HJ, Galleway FP, Galvin FC, Gowers L, Haughan AF, Lowe C, Meissner JW, Montana JG, Morgan T, Picken CL, Watson RJ. Synthesis and structure-activity relationships of guanine analogues as phosphodiesterase 7 (PDE7) inhibitors. Bioorg Med Chem Lett, 2001; 11:1081-3. https://doi.org/10.1016/S0960-894X(01)00125-1

Charaya N, Pandita D, Grewal AS, Lather V. Design, synthesis and biological evaluation of novel thiazol-2-yl benzamide derivatives as glucokinase activators. Comput Biol Chem, 2018; 73:221-29. https://doi.org/10.1016/j.compbiolchem.2018.02.018

Cunha S, Oliveira SM, Rodrigues MT Jr., Bastos RM, Ferrari J, de Oliveira CMA, Kato L, Napolitano HB, Vencato I, Lariucci C. Structural studies of 4-aminoantipyrine derivatives. J Mol Struct, 2005; 752:32-9. https://doi.org/10.1016/j.molstruc.2005.05.016

da Silva CM, da Silva DL, Modolo LV, Rosemeire BA, Alves Resende B, de Resende MA, Martins CVB, de Fatima A. Schiff bases: : A short review of their antimicrobial activities. J Adv Res, 2011; 2(1):1-8. https://doi.org/10.1016/j.jare.2010.05.004

Gaber M, El-Ghamry HA, Fathalla SK, Mansour MA. Synthesis, spectroscopic, thermal and molecular modeling studies of Zn2+, Cd2+ and UO2 2+ complexes of Schiff bases containing triazole moiety.Antimicrobial, anticancer, antioxidant and DNA binding studies. Mater Sci Eng C Mater Biol Appl, 2018; 83:78-89. https://doi.org/10.1016/j.msec.2017.11.004

Gil C, Campillo NE, Perez DI, Martinez A. PDE7 inhibitors as new drugs for neurological and infl ammatory disorders. Expert Opin Ther Patents, 2008; 18(10):1127-39. https://doi.org/10.1517/13543776.18.10.1127

Grewal AS, Sharma N, Singh S, Arora S. In silico designing of novel thiazolidine-2-one derivatives as dual PDE4/7 inhibitors for inflammatory disorders. J Pharm Technol Res Mgmt, 2017a; 5(2):149-62. https://doi.org/10.15415/jptrm.2017.52010

Grewal AS, Kumar P, Dua JS, Lather V. Synthesis, docking and anti-inflammatory activity of some newer triazole derivatives as potential PDE7 inhibitors. J Med Chem Toxicol, 2017b; 2(2):55-61. https://doi.org/10.15436/2575-808X.17.1392

Hörl WH. Nonsteroidal Anti-Inflammatory Drugs and the Kidney. Pharmaceuticals, 2010; 3:2291-321. https://doi.org/10.3390/ph3072291

Jawher V, Al-Baytii NS, Alshirayda HAY. Synthesis, spectroscopic and antibacterial investigation of new molecular hybridized 4-aminoantipyrine derivatives of pharmaceutical interest. Tikrit J Pharm Sci, 2011; 7(2):152-61.

Lagorce D, Bouslama L, Becot J, Miteva MA, Villoutreix BO. FAF-Drugs4: Free ADME-Tox filtering computations for chemical biology and early stages drug discovery. Bioinformatics, 2017; 33:3658-60. https://doi.org/10.1093/bioinformatics/btx491

Lorthiois E, Bernardelli P, Vergne F, Oliveira C, Mafroud AK, Proust E, Heuze L, Moreau F, Idrissi M, Tertre A, Bertin B, Coupe M, Wrigglesworth R, Descours A, Soulard P, Berna P. Spiroquinazolinones as novel, potent, and selective PDE7 inhibitors. Part 1. Bioorg Med Chem Lett, 2004; 14:4623-6. https://doi.org/10.1016/j.bmcl.2004.07.011

Malik MA, Dar OA, Gull P, Wani MY, Hashmi AA. Heterocyclic Schiff base transition metal complexes in antimicrobial and anticancer chemotherapy. Med ChemComm, 2018; 9(3):409-36. https://doi.org/10.1039/C7MD00526A

rapy. Med ChemComm, 2018; 9(3):409-36. Miteva MA, Guyon F, Tufféry P. Frog2: Efficient 3D conformation ensemble generator for small compounds. Nucleic Acids Res, 2010; 38:W622-7. https://doi.org/10.1093/nar/gkq325

Mohanram I, and Meshram J. Synthesis and biological activities of 4-aminoantipyrine derivatives derived from Betti-type reaction. ISRN Org Chem 2014; 2014:639392. https://doi.org/10.1155/2014/639392

Morris GM., Huey R, Lindstrom W, Sanner MF, Belew RK, Goodsell, DS, Olson AJ. Autodock4 and AutoDockTools4: automated docking with selective receptor flexibility. J Comput Chem, 2009; 16: 2785-91. https://doi.org/10.1002/jcc.21256

Murtaza S, Akhtar MS, Kanwal F, Abbas A, Ashiq S, Shamim S. Synthesis and biological evaluation of schiff bases of 4-aminophenazone as an anti-inflammatory, analgesic and antipyretic agent. J Saudi Chem Soc, 2017; 21:S359-72. https://doi.org/10.1016/j.jscs.2014.04.003

Rainsford KD. Anti-inflammatory drugs in the 21st century. In: Harris RE (ed.). Inflammation in the pathogenesis of chronic diseases: the COX-2 controversy. Springer, Dordrecht, The Netherlands, pp 3-27, 2007. https://doi.org/10.1007/1-4020-5688-5_1

Rakesh KP, Manukumar HM, Gowda DC. Schiff's bases of quinazolinone derivatives: synthesis and SAR studies of a novel series of potential anti-inflammatory and antioxidants. Bioorg Med Chem Lett, 2015; 25(5):1072-7. https://doi.org/10.1016/j.bmcl.2015.01.010

Redondo M, Brea J, Perez DI, Soteras I, Val C, Perez C, MoralesGarcía JA, Alonso-Gil S, Paul-Fernandez N, Martin-Alvarez R, Cadavid MI, Loza MI, Perez-Castillo A, Mengod G, Campillo NE, Martinez A, Gil C. Effect of phosphodiesterase 7 (PDE7) inhibitors in experimental autoimmune encephalomyelitis mice. Discovery of a new chemically diverse family of compounds. J Med Chem, 2012; 55:3274-84. https://doi.org/10.1021/jm201720d

Sharma H, Lather V, Grewal AS, Pandita D. Synthesis, antiinflammatory activity and docking studies of some newer 1,3-thiazolidine2,4-dione derivatives as dual inhibitors of PDE4 and PDE7. Curr ComputAid Drug Des, 2019; 15(3):225-34. https://doi.org/10.2174/1573409914666181003151528

Sondhi SM, Singh N, Kumar A, Lozach O, Meijer L. Synthesis, anti-inflammatory, analgesic and kinase (CDK-1,CDK-5 and GSK-3) inhibition activity evaluation of benzimidazole/benzoxazole derivatives and some Schiff's bases. Bioorg Med Chem, 2006; 14:3758-65. https://doi.org/10.1016/j.bmc.2006.01.054

Trott O, Olson AJ AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization and multithreading. J Comput Chem, 2010; 31:455-61. https://doi.org/10.1002/jcc.21334

Vergne F, Bernardelli P, Lorthiois E, Pham N, Proust E, Oliveira C, Mafroud AK, Royer F, Wrigglesworth R, Schellhaas J, Barvian M, Moreau F, Idrissi M, Tertre A, Bertin B, Coupe M, Berna P, Soulard P. Discovery of thiadiazoles as a novel structural class of potent and selective PDE7 inhibitors. Part 1: design, synthesis and structure-activity relationship studies. Bioorg Med Chem Lett, 2004; 14:4607-13. https://doi.org/10.1016/j.bmcl.2004.07.008

Article Metrics
482 Views 72 Downloads 554 Total

Year

Month

Related Search

By author names