Syntheses of Potential Bioactive Some New Pyrazole Derivatives Having Benzenesulfonamide Moiety

Abstract

In this article, 4-methyl-2,3-diphenyl-2,3-dihydro-1H-pyrazole and 4-(4-methyl-5-phenyl-2,5-dihydro-1H-pyrazole-1-yl) benzenesulfonamide derivatives were synthesized from the reactions of α, β-unsaturated aldehydes with phenylhydrazine hydrate and 4-sulfamoylphenylhydrazine hydrogen chloride, respectively. Following these reactions, aromatization of the compounds were achieved with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). Finally, SO2NH2 group of compound 4-(4-methyl-5-(3,4,5-trimethoxyphenyl) -1H-pyrazol-1-yl) benzenesulfonamidine was converted to the SO2NHCOEt group with propionic anhydride in the presence of Et3N. The structures of the synthesized compounds were characterized by 1H-NMR, 13C-NMR, and HRMS analysis.

Keywords

• Celecoxib
• Pyrazole
• Biologically active
• α, β-unsaturated aldehyde

Potansiyel Biyolojik Aktif Bazı Yeni Benzensülfonamid Yapısı Taşıyan Pirazol Türevlerinin Sentezleri

Abstract

Bu makalede, 4-metil-2,3-difenil-2,3-dihidro-1H-pirazol ve 4-(4-metil-5-fenil-2,5-dihidro-1H-pirazol-1-il)benzensulfonamid türevi bileşikler α,β-doymamış aldehit bileşiklerinin fenilhidrazin hidrat veya 4-sülfamoil fenil hidrazin hidrojen klorür ile tepkimelerinden elde edildi. Bu reaksiyonların takibinde bileşiklerin aromatlaştırma tepkimeleri 2,3-dikloro-5,6-disiyano-1,4-benzokinon (DDQ) ile yapıldı. Son olarak bileşik 4-(4-metil-5-(3,4,5-trimetoksifenil)-1H-pirazol-1-il)benzensulfonamidin SO2NH2 grubu Et3N varlığında propiyonik anhidrit ile SO2NHCOEt grubuna dönüştürüldü. Sentezlenen bileşiklerin yapıları 1H-NMR, 13C-NMR ve HRMS analiz yöntemleri ile karakterize edildi.

Keywords

• Pirazol
• Biyolojik aktif
• Celecoxib
• α,β-doymamış aldehit

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