Selective COX-2 inhibitors. Part 2: synthesis and biological evaluation of 4-benzylideneamino- and 4-phenyliminomethyl-benzenesulfonamides.

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Lin SJ, Tsai WJ, Chiou WF, Yang TH, Yang LM

Selective COX-2 inhibitors. Part 2: synthesis and biological evaluation of 4-benzylideneamino- and 4-phenyliminomethyl-benzenesulfonamides.

Bioorg Med Chem. 2008 Mar 1;16(5):2697-706. Epub 2007 Nov 17.

PubMed ID

18063374 [ View in PubMed

]

Abstract

Two series of 4-benzylideneamino- and 4-phenyliminomethyl-benzenesulfonamide derivatives were designed and synthesized for the evaluation as selective cyclooxygenase-2 (COX-2) inhibitors in a cellular assay using human whole blood (HWB). Extensive structure-activity relationships (SAR) were studied within these series. Several compounds were found to be novel and selective COX-2 inhibitors. Among them, the most potent and selective was 4-(3-carboxy-4-hydroxy-benzylideneamino)benzenesulfonamide (20, LA2135), (IC(50)'s for COX-1: 85.13 microM; COX-2: 0.74 microM; SI: 114.5), being more active COX-2 selective than celecoxib.

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Binding Properties

Drug	Target	Property	Measurement	pH	Temperature (°C)
Celecoxib	Prostaglandin G/H synthase 2	IC 50 (nM)	300	N/A	N/A	Details
Resveratrol	Prostaglandin G/H synthase 1	IC 50 (nM)	4120	N/A	N/A	Details
Resveratrol	Prostaglandin G/H synthase 2	IC 50 (nM)	34610	N/A	N/A	Details