Design, synthesis and pharmacological evaluation of 4-[2-alkylthio-5(4)-(4-substitutedphenyl)imidazole-4(5)yl]benzenesulfonamides as selective COX-2 inhibitors

Salimi, Mona; Ghahremani, Mohammad Hossein; Naderi, Nima; Amini, Mohsen; Salimi, Elika; Amanlou, Massoud; Abdi, Khosrou; Salehi, Raha; Shafiee, Abbas

doi:10.1111/j.1745-7254.2007.00619.x

Cited by 8 publications

(1 citation statement)

References 30 publications

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“…Recent studies have also shown that selective COX-2 inhibitors may slow the progress of Alzheimer's disease without causing gastrointestinal damage (Nivsarkar et al, 2008). 1,2-Diarylheterocycles have been extensively studied as selective COX-2 inhibitors (Ghodsi et al, 2010;Penning et al,1997;Prasit et al, 1999;Riendeau et al, 2002;Navidpour et al, 2006;Salimi et al, 2007;Zarghi et al, 2009). All these tricyclic molecules possess 1,2-diaryl substitution on a central hetero or carbocyclic ring system (Fig.…”

Section: Introductionmentioning

confidence: 99%

Design and synthesis of new 1,2-diaryl-4,5,6,7-tetrahydro-1H-benzo[d] imidazoles as selective cyclooxygenase (COX-2) inhibitors

et al. 2011

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A new series of 1,2-diaryl-4,5,6,7-tetrahydro-1H-benzo [d]imidazoles, possessing a methylsulfonyl pharmacophore, were synthesized to evaluate their biological activities as selective cyclooxygenase-2 (COX-2) inhibitors. In vitro COX-1 and COX-2 isozyme inhibition studies were carried out to acquire structure-activity relationship data with respect to the point that molecular modeling studies showed that designed compounds bind in the primary binding site such that the SO 2 Me substituent at para-position of C-2 phenyl ring inserts into the 2°pocket present in COX-2 enzyme. COX-1 and COX-2 inhibition studies showed that all compounds were selective inhibitors of the COX-2 isozyme with IC 50 values in the highly potent 0.34-0.69 lM range, and COX-2 selectivity indexes in the 52.3-163.8 range. 1-(4-Fluorophenyl)-2-(4-(methylsulfonyl)phenyl)-4,5,6,7-tetrahydro-1H-benzo[d] imidazole was identified as the most potent (IC 50 = 0.34 lM), and selective (SI = 163.8), COX-2 inhibitor among the synthesized compounds.

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