Novel 4-[5-{4-[(2-Benzylidenehydrazine)Carbonyl]phenyl}-3-(Trifluoromethyl)-1H-Pyrazol-1-yl]Benzenesulfonamides: Synthesis, Crystal Structure, Anti-Inflammatory and Ulcerogenecity Studies. (March 2016)

• Record Type: Journal Article
• Authors: Mustafa, Ghulam; Zia-ur-Rehman, Muhammad; Khan, Islam Ullah; Ishtiaq, Saiqa; Hussain, Sajjad; Arshad, Muhammad Nadeem; Asiri, Abdullah Mohammad
• Is Part Of: Journal of chemical research. Volume 40:Number 3(2016)
• Page Start: 167
• Page End: 172
• Publication Date: 2016-03
• Subjects: celecoxib -- rat paw oedema -- albino Wistar rats -- anti-inflammatory -- pyrazole; Chemistry -- Research -- Periodicals; Chemistry -- Periodicals; 540.5
• DOI: 10.3184/174751916X14552786665833
• Languages: English
• ISSNs: 1747-5198

Abstract

A series of novel 4-{5-[(2-benzylidenehydrazine)carbonyl]phenyl}-3-(trifluoromethyl)-1 H -pyrazol-1-yl]benzenesulfonamides was synthesised from 4-[1-(4-aminosulfonylphenyl)-3-(trifluoromethyl)-1 H -pyrazol-5-yl]benzoic acid (celecoxib). Initially, celecoxib was selectively oxidised. The product was then esterified and this was followed by hydrazinolysis to get the carbohydrazide. The carbohydrazide was subsequently reacted with a number of benzaldehyde derivatives to give the title compounds. These compounds were characterised by spectral and elemental analyses along with the single crystal X-ray crystallography of a representative compound. All the synthesised compounds were found active for their anti-inflammatory activity in the carrageenan-induced rat paw oedema model. A few of them possessed even greater in vivo anti-inflammatory activities when compared to the reference drug celecoxib and showed minimal or no ulcerogenic effect.