Methanesulfonamide Group at Position-4 of the C-5-Phenyl Ring of 1,5-Diarylpyrazole Affords a Potent...
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2004 Pyrazole derivatives Pyrazole derivatives R 0180 Methanesulfonamide Group at Position-4 of the C-5-Phenyl Ring of 1,5-Diarylpyrazole Affords a Potent Class of Cyclooxygenase-2 (COX-2) Inhibi- tors. — Diarylpyrazoles like (VIII) and (X) are synthesized by Claisen condensation of acetophenone (I) with ethyl acetates (II), coupling of diketones (III) with aryl hydra- zines (IV), and treatment of diarylpyrazole (V) with methanesulfonyl chloride (VII) to give the desired pharmacophores (VIII). Additionally, some parent methanesulfona- mides, e.g. (VIIIa), are N-acylated. 1,3-Diarylpyrazoles are also formed in minor quan- tities. Acetanilides (VI) can be hydrolyzed to amines (V). The 4-methanesulfonamide group provides a few potent and selective inhibitors of COX-2 with inhibitory concen- tration values up to 30 nM, cf. (VIIIa) (some yields not given). — (SINGH*, S. K.; VOBBALAREDDY, S.; SHIVARAMAKRISHNA, S.; KRISHNAMRAJU, A.; RAJJAK, S. A.; CASTURI, S. R.; AKHILA, V.; RAO, Y. K.; Bioorg. Med. Chem. Lett. 14 (2004) 7, 1683-1688; Chem. Discovery Res., Dr. Reddy's Lab. Ltd., Hyderabad 500 050, India; Eng.) — H. Hoennerscheid 33- 141
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Transcript of Methanesulfonamide Group at Position-4 of the C-5-Phenyl Ring of 1,5-Diarylpyrazole Affords a Potent...
2004 Pyrazole derivatives
Pyrazole derivativesR 0180 Methanesulfonamide Group at Position-4 of the C-5-Phenyl Ring of
1,5-Diarylpyrazole Affords a Potent Class of Cyclooxygenase-2 (COX-2) Inhibi-tors. — Diarylpyrazoles like (VIII) and (X) are synthesized by Claisen condensation of acetophenone (I) with ethyl acetates (II), coupling of diketones (III) with aryl hydra-zines (IV), and treatment of diarylpyrazole (V) with methanesulfonyl chloride (VII) to give the desired pharmacophores (VIII). Additionally, some parent methanesulfona-mides, e.g. (VIIIa), are N-acylated. 1,3-Diarylpyrazoles are also formed in minor quan-tities. Acetanilides (VI) can be hydrolyzed to amines (V). The 4-methanesulfonamide group provides a few potent and selective inhibitors of COX-2 with inhibitory concen-tration values up to 30 nM, cf. (VIIIa) (some yields not given). — (SINGH*, S. K.; VOBBALAREDDY, S.; SHIVARAMAKRISHNA, S.; KRISHNAMRAJU, A.; RAJJAK, S. A.; CASTURI, S. R.; AKHILA, V.; RAO, Y. K.; Bioorg. Med. Chem. Lett. 14 (2004) 7, 1683-1688; Chem. Discovery Res., Dr. Reddy's Lab. Ltd., Hyderabad 500 050, India; Eng.) — H. Hoennerscheid
33- 141
2004 Pyrazole derivatives
