Abstract A new series of difluoro phenyl pyrazole chalcone was prepared by utilizing PEG 400 as a catalyst and investigated for their antifungal, anti-inflammatory, and antioxidant activity. The compounds 3-[3-(4-bromo-phenyl)-1-phenyl-1 H -pyrazol-4-yl]-1-(2,4-difluloro-phenyl)-propenone ( IVc ), 1-(2,4-difluoro-phenyl)-3-[3-(4-methyl-phenyl)-1-phenyl-1 H -pyrazol-4-yl]-propenone ( IVd ), 1-(2,4-difluoro-phenyl)-3-[3-(4-methoxy-phenyl)-1-phenyl-1 H -pyrazol-4-yl]-propenone ( IVe ), and 1-(2,4-difluoro-phenyl)-3-(1,3-diphenyl-1 H -pyrazol-4-yl)-propenone ( IVg ) exhibited promising antifungal activity at MIC of 25 and 50 μg/mL against selected human pathogenic fungi. Synthesized compounds 1-(2,4-difluoro-phenyl)-3-[3-(4-methoxy-phenyl)-1-phenyl-1 H -pyrazol-4-yl]-propenone ( IVe ), 1-(2,4-difluoro-phenyl)-3-[3-(4-methyl-phenyl)-1-phenyl-1 H -pyrazol-4-yl]-propenone ( IVd ), 1-(2,4-difluoro-phenyl)-3-(1,3-diphenyl-1 H -pyrazol-4-yl)-propenone ( IVg ) and 1-(2,4-difluoro-phenyl)-3-[3-(4-fluoro-phenyl)-1-phenyl-1 H -pyrazol-4-yl]-propenone ( IVa ) showed good anti-inflammatory activities comparable to the standard drug diclofenac sodium. Compounds 1-(2,4-difluoro-phenyl)-3-[3-(4-methoxy-phenyl)-1-phenyl-1 H -pyrazol-4-yl]-propenone ( IVe ), 1-(2,4-difluoro-phenyl)-3-[3-(4-methyl-phenyl)-1-phenyl-1 H -pyrazol-4-yl]-propenone ( IVd ) and 1-(2,4-difluoro-phenyl)-3-(1,3-diphenyl-1 H -pyrazol-4-yl)-propenone ( IVg ) showed good hydrogen peroxide scavenging potential as compared to the butylated hydroxyl toluene. The conjugates 1-(2,4-difluoro-phenyl)-3-[3-(4-methoxy-phenyl)-1-phenyl-1 H -pyrazol-4-yl]-propenone ( IVe ), 1-(2,4-difluoro-phenyl)-3-(1,3-diphenyl-1 H -pyrazol-4-yl)-propenone ( IVg ), and 1-(2,4-difluoro-phenyl)-3-[3-(4-methyl-phenyl)-1-phenyl-1 H -pyrazol-4-yl]-propenone ( IVd ) found more potent than standard ascorbic acid in DPPH radical scavenging assay as well as ferrous reducing power assay. The conjugates showed good interactions with the target protein in docking study.

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作为抗真菌、抗炎和抗氧化剂的二氟苯基吡唑查尔酮缀合物的合成和药理学筛选

摘要 以PEG 400 为催化剂制备了新系列的二氟苯基吡唑查尔酮，并研究了其抗真菌、抗炎和抗氧化活性。化合物3-[3-(4-溴-苯基)-1-苯基-1H-吡唑-4-基]-1-(2,4-二氟-苯基)-丙烯酮(IVc), 1-(2 ,4-二氟-苯基)-3-[3-(4-甲基-苯基)-1-苯基-1H-吡唑-4-基]-丙烯酮 (IVd), 1-(2,4-二氟-苯基)-3-[3-(4-甲氧基-苯基)-1-苯基-1H-吡唑-4-基]-丙烯酮(IVe)和1-(2,4-二氟-苯基)-3-( 1,3-二苯基-1 H-吡唑-4-基)-丙烯酮 (IVg) 在 MIC 为 25 和 50 μg/mL 时对选定的人类致病真菌表现出有希望的抗真菌活性。合成化合物1-(2,4-二氟-苯基)-3-[3-(4-甲氧基-苯基)-1-苯基-1H-吡唑-4-基]-丙烯酮(IVe), 1-(2 , 4-二氟-苯基)-3-[3-(4-甲基-苯基)-1-苯基-1 H-吡唑-4-基]-丙烯酮 (IVd), 1-(2,4-二氟-苯基) -3-(1,3-二苯基-1H-吡唑-4-基)-丙烯酮(IVg)和1-(2,4-二氟-苯基)-3-[3-(4-氟-苯基)- 1-苯基-1 H-吡唑-4-基]-丙烯酮 (IVa) 显示出与标准药物双氯芬酸钠相当的良好抗炎活性。化合物 1-(2,4-二氟-苯基)-3-[3-(4-甲氧基-苯基)-1-苯基-1H-吡唑-4-基]-丙烯酮 (IVe), 1-(2, 4-二氟-苯基)-3-[3-(4-甲基-苯基)-1-苯基-1H-吡唑-4-基]-丙烯酮(IVd)和1-(2,4-二氟-苯基) -3-(1,3-二苯基-1H-吡唑-4-基)-丙烯酮(IVg)与丁基化羟基甲苯相比显示出良好的过氧化氢清除潜力。缀合物1-(2,4-二氟-苯基)-3-[3-(4-甲氧基-苯基)-1-苯基-1H-吡唑-4-基]-丙烯酮(IVe)，1-(2 , 4-二氟-苯基)-3-(1,3-二苯基-1H-吡唑-4-基)-丙烯酮(IVg)和1-(2,4-二氟-苯基)-3-[3-( 4-甲基-苯基)-1-苯基-1 H-吡唑-4-基]-丙烯酮 (IVd) 在 DPPH 自由基清除试验和亚铁还原能力试验中发现比标准抗坏血酸更有效。在对接研究中，偶联物与目标蛋白显示出良好的相互作用。