By Helmut Buschmann; Gregor Bahrenberg; et al
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Additional info for Analgesics : from chemistry and pharmacology to clinical application
American Home Products), 1998b; Kreft et al. , 2000). 7 ^M COX-1: IC50 COX-1: IC50 = 23 |uM Figure 12: Modification of etodolac. , 1999, (Merck Frosst), 1999). Optimal selectivity was conferred by a 3-atom lipophilic substitution at the 3' position of the unsubstituted phenyl ring. , 2000). 41 jiM Figure 13: Modification of flurbiprofen. , 1997). New attempts to modify the modestly selective COX-2 inhibitor led to a new series of isoquinoline-1,3-diones, which are orally active COX-2-selective inhibitors (Lazer et al.
APHS as an aspirin derivative Aspirin is the only known NSAID that covalently bonds to serine and inhibits COX-1 more significantly than COX-2. Many systematic structural modifications have been carried out resulting in the development of APHS characterized by a 60-fold increase in activity and a 100fold increase in selectivity for COX-2 than aspirin. , 1998a; 1998b). 8|LiM COX-1: IC50= 17 nM Figure 15: Modification of aspirin. Compounds with Antioxidative Moieties The mode of action of these compounds, which are under investigation, Is via an antioxidative mechanism.
Substitution at position 4 of one of the aromatic systems with a sulfonamide or a methylsulfonyl group Is essential for COX Inhibition. Replacement of the methylsulfonyl group by a sulfonamide group reduces COX-2 selectivity but improves oral bioavailability. g. pyrrole, thiazole, °xaz°'e. furane, furanone, imidazole, isoxazole, pyrimidine, thiophene, pyrazole, cyclopentenone O — S-NH2 6 R ~S-CH3 • 6 Scheme 3: General structure of carbocycles and heterocycles with vicinal aryl substituents. The structural pre-requisites shown are obligatory for enhanced activity towards COX-2.