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Synthesis, characterization and antibacterial activity of 1‐([6‐bromo‐2‐hydroxy‐naphthalen‐1‐yl]arylphenyl)methyl)‐3‐chloro‐4‐(arylphenyl)‐azetidin‐2‐one
Journal of Heterocyclic Chemistry ( IF 2.4 ) Pub Date : 2020-07-19 , DOI: 10.1002/jhet.4056
Himani N. Chopde 1 , Chandrashekhar P. Pandhurnekar 2 , Babita G. Yadao 1 , Doyel M. Bhattacharya 1 , Arvind J. Mungole 3
Affiliation  

One‐pot synthesis of 1‐([6‐bromo‐2‐hydroxy‐naphthalen‐1‐yl]‐aryl‐phenyl)methyl)‐3‐chloro‐4‐(aryl‐phenyl)azetidin‐2‐ones has been reported in the present research work via Staudinger [2 + 2] ketene‐imine cycloaddition reaction pathway. The reaction of 1‐((Benzylideneamino)(aryl)methyl)‐6‐bromo‐naphthalen‐2‐ols with chloroacetic acid and triethylamine afforded 1‐([6‐bromo‐2‐hydroxynaphthalen‐1‐yl]aryl‐phenyl)methyl)‐3‐chloro‐4‐(aryl‐phenyl)azetidin‐2‐ones. For the structural elucidation of series of compounds, different analytical and spectroscopic techniques such as elemental analysis, IR spectra, 1H‐NMR spectra and mass spectra were used. All the newly synthesized compounds were tested for their anti‐bacterial activity studies. It revealed that some of the compounds possesses moderate to good activities as compared to standard drugs. The widest spectrum of anti‐bacterial activities against both gram‐positive and gram‐negative bacterial strains among the examined compounds possessed having more hydroxyl group along with β‐lactam ring compared to other substituted azetidinones.

中文翻译:

1-([[6-溴-2--2-羟基-萘-1-基]芳基苯基)甲基)-3-氯-4-(芳基苯基)氮杂环丁烷-2-酮的合成,表征和抗菌活性

据报道一锅合成1-([6-溴-2-羟基萘-1-基]-芳基-苯基)甲基)-3-氯-4-(芳基-苯基)氮杂环丁烷-2-酮通过Staudinger [2 + 2]烯酮-亚胺环加成反应途径进行了本研究。1-((苄叉基氨基)(芳基)甲基)-6-溴萘-2-醇与氯乙酸和三乙胺的反应得到1-([6-6-溴-2-羟基萘-1-基]芳基-苯基)甲基)-3-氯-4-(芳基苯基)氮杂环丁烷-2-酮。为了阐明一系列化合物的结构,采用了不同的分析和光谱技术,例如元素分析,IR光谱,1使用了H-NMR光谱和质谱。测试了所有新合成的化合物的抗菌活性。结果表明,与标准药物相比,某些化合物具有中等至良好的活性。与其他取代的氮杂环丁酮类化合物相比,在所研究的化合物中,针对革兰氏阳性和革兰氏阴性细菌菌株的最广泛的抗菌活性具有更大的羟基和β-内酰胺环。
更新日期:2020-09-08
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