title: Design, synthesis, characterization and in vitro and in vivo anti-inflammatory evaluation of novel pyrazole-based chalcones.
abstract: Abstract A series of novel pyrazole-based chalcones have been designed, synthesized from 1-methyl-5-(2,4,6-trimethoxyphenyl)-1H-pyrazole (6). The structures of regioisomers 6 and 7 were determined by 2D (1)H-(1)H COSY, (1)H-(13)C HSQC and (1)H-(13)C HMBC experiments. The newly synthesized compounds were tested for their inhibitory activity against COX-1 and COX-2 using an in vitro cyclooxygenase (COX) inhibition assay. Moreover, they were investigated in vivo for their anti-inflammatory activities using carrageenan-induced rat paw edema model for acute inflammation and cotton pellet-induced granuloma model for chronic inflammation. All the synthesized compounds showed potential to demonstrate anti-inflammatory activities, of particular interest compounds 10i, 10e, 10f, and 10h were found to be potent anti-inflammatory agents.
authors.affiliation: Department of Organic Chemistry, Ratnagiri Sub-Centre, University of Mumbai , Ratnagiri, Maharashtra , India and.
authors.forename: Hemant V
authors.initials: HV
authors.lastname: Chavan
authors.forename: Laxman K
authors.initials: LK
authors.lastname: Adsul
authors.forename: Amol S
authors.initials: AS
authors.lastname: Kotmale
authors.forename: Valmik D
authors.initials: VD
authors.lastname: Dhakane
authors.forename: Vishnu N
authors.initials: VN
authors.lastname: Thakare
authors.forename: Babasaheb P
authors.initials: BP
authors.lastname: Bandgar
mesh_terms: D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002351:Carrageenan; D047188:Chalcones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D032561:Cotton Fiber; D051545:Cyclooxygenase 1 / Q000737:chemistry; D051546:Cyclooxygenase 2 / Q000737:chemistry; D016861:Cyclooxygenase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015195:Drug Design; D004487:Edema / Q000139:chemically induced / Q000188:drug therapy* / Q000201:enzymology / Q000473:pathology; D006099:Granuloma / Q000139:chemically induced / Q000188:drug therapy* / Q000201:enzymology / Q000473:pathology; D006614:Hindlimb; D008565:Membrane Proteins / Q000737:chemistry; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D051381:Rats; D013237:Stereoisomerism
chemical_list: D000894:Anti-Inflammatory Agents, Non-Steroidal; D047188:Chalcones; D016861:Cyclooxygenase Inhibitors; D008565:Membrane Proteins; D011720:Pyrazoles; D002351:Carrageenan; D051545:Cyclooxygenase 1; D051546:Cyclooxygenase 2; C496513:Ptgs1 protein, rat; C489691:Ptgs2 protein, rat
keywords: Anti-inflammatory activity; COSY; HMBC; HSQC; chalcone; pyrazole