title: Synthesis, anti-inflammatory and antimicrobial evaluation of novel 1-acetyl-3,5-diaryl-4,5-dihydro (1H) pyrazole derivatives bearing urea, thiourea and sulfonamide moieties.
abstract: A series of novel 1-acetyl-3-(3,4-dimethoxypheny)-5-(4-(3-(arylureido/arylthioureido/arylsulfonamido) phenyl)-4,5-dihydropyrazole derivatives of biological interest have been prepared by sequential cyclization of 1-(4-nitrophenyl)-3-(3,4-dimethoxyphenyl)-pro-2-ene-1 with hydrazine hydrate, reduction followed by reaction of resulting amine with different arylisocyanates or arylisothiocyanates or arylsulfonyl chlorides. All the synthesized compounds (1-32) have been screened for their pro-inflammatory cytokines (TNF-α and IL-6) and antimicrobial activity (antibacterial and antifungal). Biological evaluation study showed, the compounds 4, 5, 9, 11, 14 and 16 found to have promising anti-inflammatory activity (up to 61-85% TNF-α and 76-93% IL-6 inhibitory activity) at concentration of 10 μM with reference to standard dexamethasone (76% TNF-α and 86% IL-6 inhibitory activity at 1 μM). Compounds 24, 26, 27, 28 and 29 exhibited promising antimicrobial activity at MIC values ranging from 70 to 10 μg/mL against all the selected pathogenic bacteria and fungi.
authors.affiliation: Department of Chemistry, Maharashtra Udaygiri Mahavidayla, Udgir, India.
authors.forename: Ashish P
authors.initials: AP
authors.lastname: Keche
authors.forename: Girish D
authors.initials: GD
authors.lastname: Hatnapure
authors.forename: Rajesh H
authors.initials: RH
authors.lastname: Tale
authors.forename: Atish H
authors.initials: AH
authors.lastname: Rodge
authors.forename: Vandana M
authors.initials: VM
authors.lastname: Kamble
mesh_terms: D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000494:pharmacology; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects*; D005658:Fungi / Q000187:drug effects*; D008826:Microbial Sensitivity Tests; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D013449:Sulfonamides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013890:Thiourea / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D014508:Urea / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000890:Anti-Infective Agents; D000893:Anti-Inflammatory Agents; D011720:Pyrazoles; D013449:Sulfonamides; C031280:pyrazole; D014508:Urea; D013890:Thiourea