Holla Bantwal Shivarama, Mahalinga Manjathuru, Karthikeyan Mari Sithambaram, Poojary Boja, Akberali Padiyath Mohammed, Kumari Nalilu Suchetha
Department of Chemistry, Mangalore University, Mangalagangothri 574199, India.
Eur J Med Chem. 2005 Nov;40(11):1173-8. doi: 10.1016/j.ejmech.2005.02.013. Epub 2005 Jun 24.
Two substituted 1,2,3-triazoles 4 and 6 have been synthesized by the 1,3-dipolar cycloaddition reaction of 4-azido-8-(trifluoromethyl)quinoline 2 with ethyl acetoacetate and acetylacetone, respectively. The reaction of 2 with ethyl acetoacetate afforded 1-[8-(trifluoromethyl)quinolin-4-yl]-5-methyl-1H-1,2,3-triazole-4-carboxylic acid 3 and with acetylacetone afforded 1-{1-[8-(trifluoromethyl)quinolin-4-yl]-5-methyl-1H-1,2,3-triazol-4-yl}ethanone 5. Compound 3 is converted into its corresponding acid hydrazide and then condensed with different aromatic aldehydes to yield Schiff's base, N-[1-arylmethylene]-1-[8-(trifluoromethyl)quinolin-4-yl]-5-methyl-1H-1,2,3-triazole-4-carbohydrazides 4. Compound 5 is condensed with aromatic aldehydes to obtain [1-aryl-4-{1-[8-(trifluoromethyl)quinolin-4-yl]-5-methyl-1H-1,2,3-triazol-4-yl}prop-2-en-1-ones 6. The newly prepared 1,2,3-triazole derivatives 4 and 6 have been characterized by IR, NMR and mass spectral data. These compounds were screened for their antimicrobial activity.
分别通过4-叠氮基-8-(三氟甲基)喹啉2与乙酰乙酸乙酯和乙酰丙酮的1,3-偶极环加成反应合成了两种取代的1,2,3-三唑4和6。2与乙酰乙酸乙酯反应得到1-[8-(三氟甲基)喹啉-4-基]-5-甲基-1H-1,2,3-三唑-4-羧酸3，与乙酰丙酮反应得到1-{1-[8-(三氟甲基)喹啉-4-基]-5-甲基-1H-1,2,3-三唑-4-基}乙酮5。化合物3转化为其相应的酰肼，然后与不同的芳香醛缩合生成席夫碱N-[1-芳基亚甲基]-1-[8-(三氟甲基)喹啉-4-基]-5-甲基-1H-1,2,3-三唑-4-碳酰肼4。化合物5与芳香醛缩合得到[1-芳基-4-{1-[8-(三氟甲基)喹啉-4-基]-5-甲基-1H-1,2,3-三唑-4-基}丙-2-烯-1-酮6。新制备的1,2,3-三唑衍生物4和6已通过红外光谱、核磁共振光谱和质谱数据进行了表征。对这些化合物的抗菌活性进行了筛选。
