Synthesis and biological evaluation of 2,3-diarylpyrazines and quinoxalines as selective COX-2 inhibitors

“…IR spectra showed bands at 1375 and 1380 cm -1 , respectively, corresponding to the bending vibration of the terminal methyl group [34] in addition to bands at 3450 and 3400 cm -1 , respectively, due to NH group and bands at 1690-1650 cm -1 due to C=O groups. 1 H NMR spectrum showed a singlet signal at δ 2.38 ppm corresponding to the terminal methyl group protons and the absence of the vinylic proton. Dehydration of compounds 3a,b in acetic anhydride/sulphuric acid mixture gave the required compounds 9a,b .…”

Section: Chemistrymentioning

confidence: 99%

“…Quinoxaline ring system represents the building block of many biologically active compounds that possess antiinflammatory [1,2], antibacterial [3][4][5], antifungal [6], anticancer [7,8], antimalarial [9], CNS depressant [10] and hypoglycemic [11] activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel 3,4-dihydroquinoxalin-2(1H)-one derivatives

2011

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KEYWORDSNew derivatives of 3,4-dihydroquinoxaline-2(1H)-one were synthesized and characterized. Representative examples were evaluated for their antimicrobial and antifungal activities using Tetracycline and Nystatin as reference compound. One of the tested compounds 10a was found to exhibit slight activity against Staphylococcus aureus. Compounds 10b, 11b and 14b showed slight activity against Escherichia coli. Moreover, nineteen compounds were screened for their inhibition effect on CDK5, CK1, and GSK-3β. None of the tested compounds showed an inhibition activity below 10 µM concentration.Quinoxaline 3,4-dihydroquinoxalin Antimicrobial activity CK1 inhibitors CDK5 inhibitors GSK-3β inhibitors

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“…1,2-Diketone 9 was prepared as previously reported method (Singh et al, 2004). Accordingly, 1-(4-(methylthio)phenyl)-2-phenylethanone 7 was prepared by a Friedel-Craft reaction of phenylacetylchloride and thioanisole using AlCl 3 as catalyst.…”

Section: Chemistrymentioning

confidence: 99%

Design and synthesis of new 2,4,5-triarylimidazole derivatives as selective cyclooxygenase (COX-2) inhibitors

2011

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A new group of 2,4,5-triarylimidazole derivatives, possessing a methyl sulfonyl pharmacophore, were synthesized and their biological activities were evaluated for cyclooxygenase-2 (COX-2) inhibitory activity. In vitro COX-1/COX-2 structure-activity relationships were determined by varying the substituents at the para position of C-2 phenyl ring. Among the 2,4,5-triarylimidazoles, 2-(4-hydroxy phenyl)-4-(4-methylsulfonylphenyl)-5-phenyl-1H imidazole (11f) was identified as a selective COX-2 inhibitor (COX-2 IC50 = 0.15 lM; selectivity index = 75) that was less potent than the reference drug celecoxib (COX-2 IC50 = 0.06 lM; SI = 405). A molecular modeling study where 11f was docked in the binding site of COX-2 showed that the methylsulfonyl pharmacophore group is oriented in the vicinity of the COX-2 secondary pocket (Arg 513 , Phe 518 , Gly 519 , and Val 523 ). The structure-activity data acquired indicate that COX-1/COX-2 inhibition is sensitive to the nature of the C-2 phenyl substituents.

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Synthesis and biological evaluation of 2,3-diarylpyrazines and quinoxalines as selective COX-2 inhibitors

Cited by 66 publications

References 42 publications

Synthesis of tetraaryl- and tetraalkenylpyrazines by Suzuki–Miyaura reactions of tetrachloropyrazine

Synthesis of tetraaryl- and tetraalkenylpyrazines by Suzuki–Miyaura reactions of tetrachloropyrazine

Synthesis of novel 3,4-dihydroquinoxalin-2(1H)-one derivatives

Design and synthesis of new 2,4,5-triarylimidazole derivatives as selective cyclooxygenase (COX-2) inhibitors

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