N-acetyl-2-carboxy Benzenesulfonamide

Description

N-acetyl-2-carboxy Benzenesulfonamide is a structural analog of aspirin that acts as a non-selective inhibitor of cyclooxygenase (COX) with a COX-2 selectivity index of 0.23. In vitro studies showed that N-acetyl-2-carboxy Benzenesulfonamide is a more potent inhibitor of COX-1/COX-2 with IC₅₀ values of 0.06 μM and 0.25 μM, respectively, than aspirin with IC₅₀ values of 0.35 μM and 2.4 μM, respectively.

in vitro

previous in-vitro cox-1/cox-2 inhibition studies showed that n-acetyl-2-carboxy benzenesulfonamide was a more potent inhibitor than aspirin, and like aspirin. moreover, n-acetyl-2-carboxy benzenesulfonamide was found to be a nonselective cox-2 inhibitor. in addition, the molecular modeling (docking) study demonstrated that the so2nhcoch3 substituent present in n-acetyl-2-carboxy benzenesulfonamide, like the acetoxy substituent in aspirin, was suitably positioned to acetylate the ser530 hydroxyl group in the cox-2 primary binding site [1].

in vivo

animal study showed that n-acetyl-2-carboxy benzenesulfonamide and its c-4 2,4-difluorophenyl derivative had superior antiinflammatory activity (oral dosing) in a carrageenan-induced rat paw edema assay compared to aspirin. in addition, n-acetyl-2-carboxy benzenesulfonamide and its c-4 2,4-difluorophenyl derivative exhibited comparable analgesic activity to iflunisal, and superior analgesic activity compared to aspirin [1].

IC 50

0.06 and 0.25 μm for cox-1 and cox-2, respectively

References

[1] chen, q. h.,rao, p.n.p., and knaus, e.e. design, synthesis, and biological evaluation of n-acetyl-2-carboxybenzenesulfonamides: a novel class of cyclooxygenase-2 (cox-2) inhibitors. bioorganic & medicinal chemistry 13, 2459-2468 (2005).

Raw materials

Preparation Products