New pyrazole derivatives: Synthesis, anti-inflammatory activity, cycloxygenase inhibition assay and evaluation of mPGES

Serhan, 2017, Treating inflammation and infection in the 21st century: new hints from decoding resolution mediators and mechanisms, FASEB J., 31, 1273, 10.1096/fj.201601222R Poetker, 2010, A comprehensive review of the adverse effects of systemic corticosteroids, Otolaryngol. Clin., 43, 753, 10.1016/j.otc.2010.04.003 Day, 2013, Non-steroidal anti-inflammatory drugs (NSAIDs), BMJ, 346, f3195 Harirforoosh, 2013, Adverse effects of nonsteroidal antiinflammatory drugs: an update of gastrointestinal, cardiovascular and renal complications, J. Pharm. Pharm. Sci., 16, 821, 10.18433/J3VW2F Rao, 2010, Nonsteroidal anti-inflammatory drugs (NSAIDs): progress in small molecule drug development, Pharmaceuticals, 3, 1530, 10.3390/ph3051530 Rouzer, 2009, Cyclooxygenases: structural and functional insights, J. Lipid Res., 50, S29, 10.1194/jlr.R800042-JLR200 Seibert, 1994, Role of inducible cyclooxygenase (COX-2) in inflammation, Receptor, 4, 17 Flower, 2003, The development of COX2 inhibitors, Nat. Rev. Drug Discov., 2, 179, 10.1038/nrd1034 Meyer-Kirchrath, 2000, Cyclooxygenase-2 inhibition and side-effects of non-steroidal anti-inflammatory drugs in the gastrointestinal tract, Curr. Med. Chem., 7, 1121, 10.2174/0929867003374219 Martínez-González, 2007, Mechanisms underlying the cardiovascular effects of COX-inhibition: benefits and risks, Curr. Pharmaceut. Des., 13, 2215, 10.2174/138161207781368774 Park, 2006, Prostaglandin E2 synthesis and secretion: the role of PGE2 synthases, Clin. Immunol., 119, 229, 10.1016/j.clim.2006.01.016 Nakanishi, 2013, Multifaceted roles of PGE2 in inflammation and cancer, Semin. Immunopathol., 35, 123, 10.1007/s00281-012-0342-8 Chen, 2015, Targeting microsomal prostaglandin E 2 synthase-1 (mPGES-1): the development of inhibitors as an alternative to non-steroidal anti-inflammatory drugs (NSAIDs), Medchemcomm, 6, 2081, 10.1039/C5MD00278H Khurana, 2016, Chemistry and biology of microsomal prostaglandin E 2 synthase-1 (mPGES-1) inhibitors as novel anti-inflammatory agents: recent developments and current status, RSC Adv., 6, 28343, 10.1039/C5RA25186A Faria, 2017, Recently reported biological activities of pyrazole compounds, Bioorg. Med. Chem., 25, 5891, 10.1016/j.bmc.2017.09.035 Karrouchi, 2018, Synthesis and pharmacological activities of pyrazole derivatives: a review, Molecules, 23, 134, 10.3390/molecules23010134 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 Abd-El Gawad, 2012, Design and synthesis of some pyrazole derivatives of expected anti-inflammatory and analgesic activities, Med. Chem. Res., 21, 983, 10.1007/s00044-011-9606-4 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 Penning, 1997, Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: identification of 4-[5-(4-methylphenyl)-3- (trifluoromethyl)-1 H -pyrazol-1-yl]benzenesulfonamide (SC-58635, celecoxib), J. Med. Chem., 40, 1347, 10.1021/jm960803q Abdellatif, 2018, Non-acidic 1,3,4-trisubstituted-pyrazole derivatives as lonazolac analogs with promising COX-2 selectivity, anti-inflammatory activity and gastric safety profile, Bioorg. Chem., 77, 568, 10.1016/j.bioorg.2018.02.018 Ren, 2018, Design and biological evaluation of novel hybrids of 1, 5-diarylpyrazole and Chrysin for selective COX-2 inhibition, Bioorg. Med. Chem., 26, 4264, 10.1016/j.bmc.2018.07.022 Ghareb, 2017, Novel pyrazoles and pyrazolo[1,2-a]pyridazines as selective COX-2 inhibitors; Ultrasound-assisted synthesis, biological evaluation, and DFT calculations, Bioorg. Med. Chem. Lett, 27, 2377, 10.1016/j.bmcl.2017.04.020 Pavase, 2018, Anti-inflammatory exploration of sulfonamide containing diaryl pyrazoles with promising COX-2 selectivity and enhanced gastric safety profile, J. Heterocycl. Chem., 55, 913, 10.1002/jhet.3118 Abdel-Aziz, 2014, Synthesis of N-benzenesulfonamide-1H-pyrazoles bearing arylsulfonyl moiety: novel celecoxib analogs as potent anti-inflammatory agents, Eur. J. Med. Chem., 80, 416, 10.1016/j.ejmech.2014.04.065 Ashour, 2016, Synthesis and pharmacological evaluation of new pyrazolyl benzenesulfonamides linked to polysubstituted pyrazoles and thiazolidinones as anti-inflammatory and analgesic agents, Monatshefte Für Chemie - Chem. Mon., 147, 605, 10.1007/s00706-015-1549-x Sai Ram, 2006, Ligand coordinate analysis of SC-558 from the active site to the surface of COX-2: a molecular dynamics study, J. Chem. Inf. Model., 46, 1784, 10.1021/ci050142i Mohy El-Din, 2011, A novel COX-2 inhibitor pyrazole derivative proven effective as an anti-inflammatory and analgesic drug, Basic Clin. Pharmacol. Toxicol., 108, 263, 10.1111/j.1742-7843.2010.00648.x Barsoum, 2009, Facile synthesis of bis(4,5-dihydro-1H-pyrazole-1-carboxamides) and their thio-analogues of potential PGE2 inhibitory properties, Eur. J. Med. Chem., 44, 2172, 10.1016/j.ejmech.2008.10.020 Ram, 1979, Pyrazoles and pyrazolo[3,4-d]pyrimidines as biologically active agents, II, Arch. Pharm. (Weinheim), 312, 703, 10.1002/ardp.19793120810 Hunsberger, 1956, The preparation of substituted hydrazines. IV. Arylhydrazines via conventional methods, J. Org. Chem., 21, 394, 10.1021/jo01110a004 E. Widiarini, Organic Chemistry, fourth ed., Francis A. Carey, (n.d.). Xavier, 2014 Silverstein, 2014 Murakami, 2000, Regulation of prostaglandin E2 biosynthesis by inducible membrane-associated prostaglandin E2 synthase that acts in concert with cyclooxygenase-2, J. Biol. Chem., 275, 32783, 10.1074/jbc.M003505200 Murakami, 2003, Cellular prostaglandin E2 production by membrane-bound prostaglandin E synthase-2 via both cyclooxygenases-1 and-2, J. Biol. Chem., 278, 37937, 10.1074/jbc.M305108200 Wobst, 2008, Dimethylcelecoxib inhibits prostaglandin E2 production, Biochem. Pharmacol., 76, 62, 10.1016/j.bcp.2008.04.008 Koeberle, 2009, Inhibitors of the microsomal prostaglandin E2 synthase-1 as alternative to non steroidal anti-inflammatory drugs (NSAIDs)-a critical review, Curr. Med. Chem., 16, 4274, 10.2174/092986709789578178 Deckmann, 2010, Dimethylcelecoxib inhibits mPGES-1 promoter activity by influencing EGR1 and NF-κB, Biochem. Pharmacol., 80, 1365, 10.1016/j.bcp.2010.07.032 Meade, 1993, Differential inhibition of prostaglandin endoperoxide synthase (cyclooxygenase) isozymes by aspirin and other non-steroidal anti-inflammatory drugs, J. Biol. Chem., 268, 6610, 10.1016/S0021-9258(18)53294-4 Garavito, 1999, The cyclooxygenase isoforms: structural insights into the conversion of arachidonic acid to prostaglandins, Biochim. Biophys. Acta Mol. Cell Biol. Lipids, 1441, 278, 10.1016/S1388-1981(99)00147-X Orlando, 2016, Substrate-selective inhibition of cyclooxygeanse-2 by fenamic acid derivatives is dependent on peroxide tone, J. Biol. Chem., 291, 15069, 10.1074/jbc.M116.725713 Xu, 2014, Oxicams bind in a novel mode to the cyclooxygenase active site via a two-water-mediated H-bonding network, J. Biol. Chem., 289, 6799, 10.1074/jbc.M113.517987 Kurumbail, 1996, Structural basis for selective inhibition of cyclooxygenase-2 by anti-inflammatory agents, Nature, 384, 644, 10.1038/384644a0 Soliva, 2003 Morris, 2009, AutoDock4 and AutoDockTools4: automated docking with selective receptor flexibility, J. Comput. Chem., 30, 2785, 10.1002/jcc.21256 Pettersen, 2004, UCSF Chimera?A visualization system for exploratory research and analysis, J. Comput. Chem., 25, 1605, 10.1002/jcc.20084 Winter, 1962, Carrageenin-induced edema in hind paw of the rat as an assay for antiinflammatory drugs, Proc. Soc. Exp. Biol. Med., 111, 544, 10.3181/00379727-111-27849 Case, 2012, Amber, 12 Word, 1999, Asparagine and glutamine: using hydrogen atom contacts in the choice of side-chain amide orientation, J. Mol. Biol., 285, 1735, 10.1006/jmbi.1998.2401 Cornell, 1995, A second generation force field for the simulation of proteins, nucleic acids, and organic molecules, J. Am. Chem. Soc., 117, 5179, 10.1021/ja00124a002 Hornak, 2006, Comparison of multiple Amber force fields and development of improved protein backbone parameters, Proteins Struct. Funct. Bioinforma., 65, 712, 10.1002/prot.21123 Wang, 2006, Automatic atom type and bond type perception in molecular mechanical calculations, J. Mol. Graph. Model., 25, 247, 10.1016/j.jmgm.2005.12.005 Wang, 2004, Development and testing of a general amber force field, J. Comput. Chem., 25, 1157, 10.1002/jcc.20035 Alaraby Salem, 2015, Two-photon absorption of fluorescent protein chromophores incorporating non-canonical amino acids: TD-DFT screening and classical dynamics, Phys. Chem. Chem. Phys., 17, 25563, 10.1039/C5CP03875H Roe, 2013, PTRAJ and CPPTRAJ: software for processing and analysis of molecular dynamics trajectory data, J. Chem. Theory Comput., 9, 3084, 10.1021/ct400341p J. Paul, XMGRACE, Version 5.1. 19. Turner Center for Coastal and Land-Margin Research Oregon Graduate Institute of Science and Technology Beaverton, Oregon. Humphrey, 1996, VMD: visual molecular dynamics, J. Mol. Graph., 14, 27