Synthesis of new thiazolo-celecoxib analogues as dual cyclooxygenase-2/15-lipoxygenase inhibitors: Determination of regio-specific different pyrazole cyclization by 2D NMR

European Journal of Medicinal Chemistry
2016.0

Abstract

Two new series of 1,5-diaryl pyrazoles (5a, 5b, 7a, 7b and 10) and 1,5-diaryl pyrazoline (12a and 12b) were prepared as both Cyclooxygenase-2 and 15-lipoxygenase inhibitors. Carrageenan-induced rat paw edema, ulcer index and anti-COX-1/COX-2 and 15-LOX inhibition assays were also included. Cyclization of different pyrazoles was discussed using 2D NMR such as HSQC, HMBC and NOSEY determinations. Compound 5a is more effective with ED50 = 0.98 and 3.98 μM against COX-2 and 15-lipoxygenase respectively, than the references celecoxib (1.54 μM) and meclofenamate sodium (5.64 μM).

Knowledge Graph

Similar Paper

Synthesis of new thiazolo-celecoxib analogues as dual cyclooxygenase-2/15-lipoxygenase inhibitors: Determination of regio-specific different pyrazole cyclization by 2D NMR
European Journal of Medicinal Chemistry 2016.0
Cyclooxygenase-2 and 15-lipoxygenase inhibition, synthesis, anti-inflammatory activity and ulcer liability of new celecoxib analogues: Determination of region-specific pyrazole ring formation by NOESY
Bioorganic & Medicinal Chemistry Letters 2016.0
Novel class of benzimidazole-thiazole hybrids: The privileged scaffolds of potent anti-inflammatory activity with dual inhibition of cyclooxygenase and 15-lipoxygenase enzymes
Bioorganic & Medicinal Chemistry 2020.0
Design, synthesis, and biological evaluation of 1-(4-sulfamylphenyl)-3-trifluoromethyl-5-indolyl pyrazolines as cyclooxygenase-2 (COX-2) and lipoxygenase (LOX) inhibitors
Bioorganic & Medicinal Chemistry 2008.0
Synthesis of Celecoxib Analogues Possessing aN-Difluoromethyl-1,2-dihydropyrid-2-one 5-Lipoxygenase Pharmacophore: Biological Evaluation as Dual Inhibitors of Cyclooxygenases and 5-Lipoxygenase with Anti-Inflammatory Activity
Journal of Medicinal Chemistry 2009.0
Synthesis, cyclooxygenase inhibition, anti-inflammatory evaluation and ulcerogenic liability of new 1,3,5-triarylpyrazoline and 1,5-diarylpyrazole derivatives as selective COX-2 inhibitors
Bioorganic & Medicinal Chemistry Letters 2016.0
Synthesis of N-benzenesulfonamide-1H-pyrazoles bearing arylsulfonyl moiety: Novel celecoxib analogs as potent anti-inflammatory agents
European Journal of Medicinal Chemistry 2014.0
Heteroaromatic analogues of 1,5-diarylpyrazole class as anti-inflammatory agents
Medicinal Chemistry Research 2012.0
Synthesis of novel hybrids of pyrazole and coumarin as dual inhibitors of COX-2 and 5-LOX
Bioorganic & Medicinal Chemistry Letters 2017.0
Synthesis, biological evaluation and molecular modeling study of pyrazole and pyrazoline derivatives as selective COX-2 inhibitors and anti-inflammatory agents. Part 2
Bioorganic & Medicinal Chemistry 2012.0