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

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dc.AffiliationOctober University for modern sciences and Arts (MSA)
dc.contributor.authorHassan G.S.
dc.contributor.authorAbdel Rahman D.E.
dc.contributor.authorAbdelmajeed E.A.
dc.contributor.authorRefaey R.H.
dc.contributor.authorAlaraby Salem M.
dc.contributor.authorNissan Y.M.
dc.contributor.otherPharmaceutical Chemistry Department
dc.contributor.otherFaculty of Pharmacy
dc.contributor.otherCairo University
dc.contributor.otherKasr Elini St.
dc.contributor.otherCairo
dc.contributor.other11562
dc.contributor.otherEgypt; Pharmaceutical Chemistry Department
dc.contributor.otherFaculty of Pharmacy
dc.contributor.otherBadr University in Cairo
dc.contributor.otherBadr City
dc.contributor.otherCairo
dc.contributor.other11829
dc.contributor.otherEgypt; National Cancer Institute
dc.contributor.otherCairo University
dc.contributor.otherFomElkhalig
dc.contributor.otherKasr Elaini St.
dc.contributor.otherCairo
dc.contributor.other11796
dc.contributor.otherEgypt; Pharmaceutical Chemistry Department
dc.contributor.otherFaculty of Pharmacy
dc.contributor.otherOctober University for Modern Sciences and Arts (MSA)
dc.contributor.otherGiza
dc.contributor.otherEgypt
dc.date.accessioned2020-01-09T20:40:37Z
dc.date.available2020-01-09T20:40:37Z
dc.date.issued2019
dc.descriptionScopus
dc.description.abstractNew pyrazole derivatives 2�5 were synthesized and evaluated for their COX-1 and COX-2 inhibitory activity in vitro. All compounds showed good inhibitory activity at a nanomolar level and most compounds exhibited selectivity towards COX-2 inhibition. Compounds 2a, 3b, 4a, 5b and 5e exhibited IC50 towards COX-2 enzyme of 19.87, 39.43, 61.24, 38.73 and 39.14 nM, respectively. Furthermore, compounds 3b, 4a, 5b and 5e exhibited a selectivity index of 22.21, 14.35, 17.47 and 13.10, respectively. The most active compounds were further subjected to in vivo anti-inflammatory assay. The tested compounds showed better or comparable activity to celecoxib as positive control. In order to explore their binding mode and selectivity behaviour, molecular docking in the active site of COX-2 was carried out for these derivatives. Analysis of the docked poses of the compounds showed that they adopt similar conformations to the highly selective COX-2 inhibitor, SC-558. The docking pose of compound 3b was confirmed by molecular dynamics. All the tested compounds exhibited potent inhibitory effect on the production of PGE2, in addition to their inhibition of COX-2 enzyme. � 2019 Elsevier Masson SASen_US
dc.description.urihttps://www.scimagojr.com/journalsearch.php?q=17464&tip=sid&clean=0
dc.identifier.doihttps://doi.org/10.1016/j.ejmech.2019.03.052
dc.identifier.doiPubMed ID 30928706
dc.identifier.issn2235234
dc.identifier.otherhttps://doi.org/10.1016/j.ejmech.2019.03.052
dc.identifier.otherPubMed ID 30928706
dc.identifier.urihttps://t.ly/JKlwY
dc.language.isoEnglishen_US
dc.publisherElsevier Masson SASen_US
dc.relation.ispartofseriesEuropean Journal of Medicinal Chemistry
dc.relation.ispartofseries171
dc.subjectBenzenesulfonamideen_US
dc.subjectmPGESen_US
dc.subjectPyrazoleen_US
dc.subjectSelective COX-2en_US
dc.subject2 chloro n [4 cyano 1 (4 sulfamoylphenyl) 1h pyrazol 5 yl]acetamideen_US
dc.subject3 chloro n [4 cyano 1 (4 sulfamoylphenyl) 1h pyrazol 5 yl]acetamideen_US
dc.subject4 [4 cyano 5 (3,5 dimethoxybenzylidene)amino 1h pyrazol 1 yl]benzene sulfonamideen_US
dc.subject4 [4 cyano 5 (4 fluorobenzylidene)amino 1h pyrazol 1 yl]benzenesulfonamideen_US
dc.subject4 [4 cyano 5 (4 methoxybenzylidene)amino 1h pyrazol 1 yl]benzene sulfonamideen_US
dc.subject4 [5 (4 bromobenzylidene)amino cyano 1h pyrazol 1 yl]benzenesulfonamideen_US
dc.subject4 [5 (4 bromophenyl) 3 trifluoromethyl 1h pyrazol 1 yl]benzenesulfonamideen_US
dc.subject4 [5 (4 chlorobenzylidene)amino cyano 1h pyrazol 1 yl]benzenesulfonamideen_US
dc.subject4 [5 (benzylidene)amino 4 cyano 1h pyrazol 1 yl]benzenesulfonamideen_US
dc.subjectantiinflammatory agenten_US
dc.subjectcelecoxiben_US
dc.subjectcyclooxygenase 1en_US
dc.subjectcyclooxygenase 1 inhibitoren_US
dc.subjectcyclooxygenase 2en_US
dc.subjectcyclooxygenase 2 inhibitoren_US
dc.subjectisoenzymeen_US
dc.subjectn [4 (5 acetamido 4 cyano 1h pyrazol 1 yl)phenyl]sulfonylacetamideen_US
dc.subjectn [4 cyano 1 (4 sulfamoylphenyl) 1h pyrazol 5 yl] 2 morpholinoacetamideen_US
dc.subjectn [4 cyano 1 (4 sulfamoylphenyl) 1h pyrazol 5 yl] 2 morpholinopropionamideen_US
dc.subjectn [4 cyano 1 (4 sulfamoylphenyl) 1h pyrazol 5 yl] 3 morpholinopropionamideen_US
dc.subjectn [4 cyano 1 (4 sulfamoylphenyl) 1h pyrazol 5 yl]benzamideen_US
dc.subjectprostaglandin E2 synthaseen_US
dc.subjectpyrazole derivativeen_US
dc.subjectsulfonamideen_US
dc.subjectunclassified drugen_US
dc.subjectcyclooxygenase 1en_US
dc.subjectcyclooxygenase 2en_US
dc.subjectnonsteroid antiinflammatory agenten_US
dc.subjectprostaglandin synthaseen_US
dc.subjectprostaglandin synthase inhibitoren_US
dc.subjectpyrazoleen_US
dc.subjectpyrazole derivativeen_US
dc.subjectanimal experimenten_US
dc.subjectanimal modelen_US
dc.subjectantiinflammatory activityen_US
dc.subjectArticleen_US
dc.subjectcarbon nuclear magnetic resonanceen_US
dc.subjectcarrageenan-induced paw edemaen_US
dc.subjectcontrolled studyen_US
dc.subjectcytosolen_US
dc.subjectdrug synthesisen_US
dc.subjectenzyme immunoassayen_US
dc.subjecthydrogen bonden_US
dc.subjectIC50en_US
dc.subjectmaleen_US
dc.subjectmicrosomeen_US
dc.subjectmolecular dockingen_US
dc.subjectmolecular dynamicsen_US
dc.subjectnonhumanen_US
dc.subjectproton nuclear magnetic resonanceen_US
dc.subjectraten_US
dc.subjectselectivity indexen_US
dc.subjectchemical structureen_US
dc.subjectchemistryen_US
dc.subjectdose responseen_US
dc.subjectdrug effecten_US
dc.subjectenzymologyen_US
dc.subjecthumanen_US
dc.subjectmetabolismen_US
dc.subjectstructure activity relationen_US
dc.subjectsynthesisen_US
dc.subjectAnti-Inflammatory Agents, Non-Steroidalen_US
dc.subjectCyclooxygenase 1en_US
dc.subjectCyclooxygenase 2en_US
dc.subjectCyclooxygenase Inhibitorsen_US
dc.subjectDose-Response Relationship, Drugen_US
dc.subjectHumansen_US
dc.subjectMicrosomesen_US
dc.subjectMolecular Docking Simulationen_US
dc.subjectMolecular Structureen_US
dc.subjectProstaglandin-Endoperoxide Synthasesen_US
dc.subjectPyrazolesen_US
dc.subjectStructure-Activity Relationshipen_US
dc.titleNew pyrazole derivatives: Synthesis, anti-inflammatory activity, cycloxygenase inhibition assay and evaluation of mPGESen_US
dc.typeArticleen_US
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