Abstract
The present work deals with the synthesis of acetoxysulfonamide pyrazole derivatives, substituted 4,5-dihydropyrazole-1-carbothioamide and 4,5-dihydropyrazole-1-isonicotinoyl derivatives starting from substituted vanillin chalcones. Acetoxysulfonamide pyrazole derivatives were prepared from the reaction of chalcones with p-sulfamylphenylhydrazine followed by treatment with acetic anhydride. At the same time 4,5-dihydropyrazole-1-carbothioamide and 4,5-dihydropyrazole-1-isonicotinoyl derivatives were prepared from the reaction of chalcones with either thiosemicarbazide or isonicotinic acid hydrazide, respectively. The synthesized compounds were structurally characterized on the basis of IR, 1H-NMR, 13C-NMR spectral data and microanalyses. All of the newly isolated compounds were tested for their antimicrobial activities. The antimicrobial screening using the agar well-diffusion method revealed that the chloro derivatives are the most active ones. Moreover, the antioxidant and anti-inflammatory activity of these chloro derivatives are also studied using the DPPH radical scavenging and NO radical scavenging methods, respectively.
Highlights
Pyrazole and its derivatives represent one of the most active classes of heterocyclic compounds possessing a wide spectrum of biological activities
As a part of our program aiming at the synthesis of different heterocyclic derivatives, we report here in the convenient synthesis of some new pyrazoles 3a–e and dihydropyrazoles 4a–e and 5a–e starting from chalcones 1a–e. which exhibit efficient antimicrobial, antioxidant and anti-inflammatory activities
All synthesized compounds were characterized by spectral data (IR, 1H-NMR and 13C-NMR) that was consistent with the proposed structures
Summary
Pyrazole and its derivatives represent one of the most active classes of heterocyclic compounds possessing a wide spectrum of biological activities. They are used as antitumor [1], antibacterial, antifungal, antiviral, antiparasitic, antitubercular, insecticidal, anti-inflammatory, antidiabetic and analgesic compounds [2,3,4,5,6,7,8,9,10,11,12,13,14]. The structure activity relationships of celecoxib attracted our attention and prompted us to synthesize some matching pyrazole derivatives with some structural modifications
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