Design, synthesis of novel isoindoline hybrids as COX-2 inhibitors: Anti-inflammatory, analgesic activities and docking study

Ulbrich, 2002, Cyclooxygenase-1/2 (COX-1/COX-2) and 5-lipoxygenase (5-LOX) inhibitors of the 6,7-diaryl-2,3–1H-dihydropyrrolizine type, Eur. J. Med. Chem., 37, 953, 10.1016/S0223-5234(02)01418-6 Michaux, 2002, A new potential cyclooxygenase-2 inhibitor, pyridinic analogue of nimesulide, Eur. J. Med. Chem., 40, 1316, 10.1016/j.ejmech.2005.08.003 Hassan, 2014, Celecoxib analogs bearing benzofuran moiety as cyclooxygenase-2 inhibitors: Design, synthesis and evaluation as potential anti-inflammatory agents, Eur. J. Med. Chem., 78, 482, 10.1016/j.ejmech.2014.02.033 Arfaie, 2010, Design, synthesis and biological evaluation of new (E)- and (Z)-1,2,3-triaryl-2-propen-1-ones as selective COX-2 inhibitors Eur, J. Med. Chem., 45, 4013, 10.1016/j.ejmech.2010.05.058 Park, 2002, Investigations of new lead structures for the design of novel cyclooxygenase-2 inhibitors, Eur. J. Med. Chem., 37, 461, 10.1016/S0223-5234(02)01373-9 Ugwu, 2018, Novel anti-inflammatory and analgesic agents: synthesis, molecular docking and in vivo studies, J. Enzyme Inhib. Med. Chem., 33, 405, 10.1080/14756366.2018.1426573 Singh, 2005, Synthesis and SAR/3D-QSAR studies on the COX-2 inhibitory activity of 1,5-diarylpyrazoles to validate the modified pharmacophore, Eur. J. Med. Chem., 40, 977, 10.1016/j.ejmech.2005.03.016 El-Araby, 2012, Design, Synthesis and in vivo anti-inflammatory activities of 2,4-diaryl-5-4h-imidazolone derivatives, Molecules, 17, 12262, 10.3390/molecules171012262 Küçükgüzel, 2013, Synthesis and characterization of celecoxib derivatives as possible anti-inflammatory, analgesic, antioxidant, anticancer and anti-HCV agents, Molecules, 18, 3595, 10.3390/molecules18033595 Anna, 2007, Structural and functional basis of cyclooxygenase inhibition, J. Med. Chem., 50, 1426 Zarghi, 2011, Selective COX-2 inhibitors: a review of their structure-activity relationships, IJPR, 10, 655 Badrey, 2015, Design and synthesis of imidazopyrazolopyridines as novel selective COX-2 inhibitors, Molecules, 20, 15287, 10.3390/molecules200815287 Ghabbour, 2016, Synthesis, crystal structure, density function theory, molecular docking and antimicrobial Studies of 2-(3-(4-phenylpiperazin-1-yl) propyl) isoindoline-1,3-dione, Trop. J. Pharm. Res., 15, 385, 10.4314/tjpr.v15i2.23 Assis, 2014, Synthesis, hypolipidemic, and anti-inflammatory activities of arylphthalimides, Med. Chem. Res., 23, 708, 10.1007/s00044-013-0673-6 Hebda, 2016, Synthesis, molecular modeling and biological evaluation of novel heterodimeric, multiple ligands targeting cholinesterases and amyloid beta, Molecules, 21, 410, 10.3390/molecules21040410 Manley-King, 2011, Inhibition of monoamine oxidase by C5-substituted phthalimide analogues, Bioorg. Med. Chem., 19, 4829, 10.1016/j.bmc.2011.06.070 Lima, 2002, Novel phthalimide derivatives, designed as leukotriene D4 receptor antagonists, Bioorg. Med. Chem. Lett., 12, 1533, 10.1016/S0960-894X(02)00203-2 Kato, 2011, Synthesis and pharmacological characterization of potent, selective, and orally bioavailable isoindoline class dipeptidyl peptidase IV inhibitors, Org. Med. Chem. Lett., 1, 7, 10.1186/2191-2858-1-7 Lamie, 2015, Design Synthesis and evaluation of novel phthalimide derivatives as in vitro anti-microbial, anti-oxidant and anti-inflammatory agents, Molecules, 20, 16620, 10.3390/molecules200916620 Pareshkumar, 2014, Synthesis and biological evaluation of some new chalcone and isoxazole derivatives, Int. J. Sci. Technoledge, 2, 138 Abu-Hashem, 2011, Synthesis, anti-inflammatory and analgesic evaluation of certain new 3a,4,9,9a-Tetrahydro-4,9-benzenobenz[f]isoindole-1,3-diones, Arch. Pharm. Chem. Life Sci., 344, 543, 10.1002/ardp.201100020 Alam, 2015, A review on pyrazole chemical entity and biological activity, Int. J. Pharm. Sci. Res., 6, 1433 Ahmed, 2016, Synthesis, characterization, molecular modeling, and potential antimicrobial and anticancer activities of novel 2-aminoisoindoline-1,3-dione derivatives, Bioorg. Chem., 66, 1, 10.1016/j.bioorg.2016.03.003 Alanazi, 2015, Structure-based design of phthalimide derivatives as potential cyclooxygenase-2 (COX-2) inhibitors: Anti-inflammatory and analgesic activities, Eur. J. Med. Chem., 92, 115, 10.1016/j.ejmech.2014.12.039 Li, 2002, Design, syntheses, and evaluation of 2,3-diphenylcycloprop-2-en-1-ones and oxime derivatives as potential cyclooxygenase-2 (COX-2) inhibitors with analgesic-antiinflammatory activity, Drug Develop. Res., 57, 6, 10.1002/ddr.10102 Abdelgawad, 2017, Pyrazole-hydrazone derivatives as anti-inflammatory agents: Design, synthesis, biological evaluation, COX-1,2/5-LOX inhibition and docking study, Bioorg. Chem., 74, 212, 10.1016/j.bioorg.2017.08.014 Mohammed, 2014, Synthesis, molecular docking, and biological evaluation of some novel hydrazones and pyrazole derivatives as anti-inflammatory agents, Chem. Biol. Drug Des., 84, 473, 10.1111/cbdd.12336 Zarghi, 2006, Synthesis and biological evaluation of 1,3- diphenylprop-2-en-1-ones possessing a methanesulfonamido or an azido pharmacophore as cyclooxygenase-1/-2 inhibitors, Bioorg. Med. Chem., 14, 7044, 10.1016/j.bmc.2006.06.022 Lorens, 2002, J. Mol. Graph. Modell., 20, 359, 10.1016/S1093-3263(01)00135-8 Abdellatif, 2015, Synthesis, cyclooxygenase inhibition, anti-inflammatory evaluation and ulcerogenic liability of novel triarylpyrazoline derivatives as selective COX-2 inhibitors, Bioorg. Med. Chem. Lett., 25, 5787, 10.1016/j.bmcl.2015.10.047 Abdellatif, 2017, Synthesis and biological evaluation of new diarylpyrazole and triarylimidazoline derivatives as selective COX-2 inhibitors, Archiv der Pharmzie, 350 Barreiro, 2002, A química medicinal de N-acilidrazonas: Novos compostos-protótipos de fármacos analgésicos, antiinflamatórios et anti-trombóticos, Quim. Nova, 25, 129, 10.1590/S0100-40422002000100022 Hamak, 2014, Synthetic of phthalimides via the reaction of phthalic anhydride with amines and evaluating of its biological and anti corrosion activity, Int. J. Chem. Tech. Res., 6, 324 Rao, 2003, Design, synthesis, and biological evaluation of 6-substituted-3-(4-methanesulfonylphenyl)-4-phenylpyran-2-ones: a novel class of diarylheterocyclic selective cyclooxygenase-2 Inhibitors, J. Med. Chem., 46, 4872, 10.1021/jm0302391 Swarup, 2016, A comparative study of efficacy of gabapentin in inflammation induced neuropathic animal pain models with conventional analgesic diclofenac, Int. J. Res. Med. Sci., 4, 1429, 10.18203/2320-6012.ijrms20161204 Arrigoni-Martelli, 1979, Screening and assessment of anti-inflammatory drugs, Methods Find Exp Clin. Pharmacol., 1, 157 Fakhr, 2009, Synthesis and pharmacological evaluation of 2-substituted benzo[b]thiophenes as anti-inflammatory and analgesic agents, Eur. J. Med. Chem., 44, 1718, 10.1016/j.ejmech.2008.02.034 Available from: http://www.rcsb.org/pdb/explore/explore.do?structureId=1CX2.