Abstract

A new series of 1-(5-(4-alkoxy-3-(methylsulfonyl)phenyl)thiophen-2-yl)-5-substituted-3-(trifluoromethyl)-1H-pyrazole have been synthesized by a cyclocondensation reaction of 1,1,1-trifluoropentane-2,4-dione (1a) with (5-(4-methoxy-3-(methylsulfonyl)phenyl)thiophen-2-yl)hydrazine (2). The structure of 1-(5-(4-alkoxy-3-(methylsulfonyl)phenyl)thiophen-2-yl)-5-substituted-3-(trifluoromethyl)-1H-pyrazole derivatives was characterized by spectroscopic analysis. The synthesized 3-(trifluoromethyl)-1H-pyrazole derivatives were screened for in vitro antibacterial activity against Escherichia coli (NCIM 2574), Proteus mirabilis (NCIM 2388) Bacillus subtilis (NCIM 2063) and Staphylococcus albus (NCIM 2178) and in vitro antifungal activity against Candida albicans (NCIM 3100) and Aspergillus niger (ATCC 504). The compounds 4-(5-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)thiophen-2-yl)-2-(methylsulfonyl)phenol (4) and 1-methyl-4-(4-(5-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)thiophen-2-yl)-2-(methylsulfonyl)phenoxy)pyrrolidin-2-one (6e) showed moderate to good antibacterial and antifungal activity.

摘要

通过 1 ,1,1-三氟戊烷-2,4-二酮 ( 1a ) 与 (5-(4-甲氧基-3-(甲基磺酰基)苯基)噻吩-2-基)肼 ( 2 )。1-(5-(4-烷氧基-3-(甲基磺酰基)苯基)噻吩-2-基)-5-取代-3-(三氟甲基)-1H-吡唑衍生物的结构通过光谱分析表征。筛选合成的 3-(三氟甲基)-1H-吡唑衍生物对大肠杆菌(NCIM 2574)、奇异变形杆菌(NCIM 2388)、枯草芽孢杆菌(NCIM 2063) 和白色葡萄球菌(NCIM 2178) 以及针对白色念珠菌(NCIM 3100) 和黑曲霉(ATCC 504) 的体外抗真菌活性。化合物 4-(5-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)thiophen-2-yl)-2-(methylsulfonyl)phenol ( 4 ) 和 1-methyl- 4- ( 4-(5-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)thiophen-2-yl)-2-(methylsulfonyl)phenoxy)pyrrolidin-2-one (6e) 表现出中等至良好抗菌和抗真菌活性。