{"title":"A novel bioactive compounds of 2-azetidinone derived from pyrazin dicarboxylic acid: synthesis and antmicrobial screening","authors":"A. Ayyash, H. Q. A. Habeeb","doi":"10.23893/1307-2080.aps.05727","DOIUrl":null,"url":null,"abstract":"A series of novel 2-azetidinons entitled N, N’-bis[3-chloro-2-oxo-4-(substituted pyridine-2-yl)-azetidin-1-yl] pyrazine-2,3-dicarboxamide and N,N’-bis[3,3-dichloro-2-oxo-4-(substitutedpyridine-2-yl)-azetidin-1-yl] pyrazine-2,3-dicarboxamide have been synthesized from the relating newly Schiff bases by [2+2] cycloaddition reaction in good yields. Starting with pyrazine-2,3-dicarboxylic acid which was converted to the corresponding diester in absolute ethanol and glacial acetic acid as a catalyst. After that, the hydazinolysis of resulted diester with hydrazine hydrate afforded dicarbohydrazide which further treated with different substituted pyridine-2-carbaldehyde to give new Schiff bases. These new Schiff bases were reacted with chloroacetochloride and (or) dichloroacetochloride in presence of trimethylamine in DMF solvent under reflux and stirring to yield new derivatives of titled compounds. The structural assignments were estimated from their spectroscopic analysis such as IR,1H NMR, 13C NMR, and C, H, N elemental analysis. The newly prepared 2-azetidinones have been screened for their antimicrobial activity and some of them revealed excellent antibacterial and antifungal activities.","PeriodicalId":6962,"journal":{"name":"ACTA Pharmaceutica Sciencia","volume":"1 1","pages":""},"PeriodicalIF":0.0000,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"3","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"ACTA Pharmaceutica Sciencia","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.23893/1307-2080.aps.05727","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"Pharmacology, Toxicology and Pharmaceutics","Score":null,"Total":0}
引用次数: 3
Abstract
A series of novel 2-azetidinons entitled N, N’-bis[3-chloro-2-oxo-4-(substituted pyridine-2-yl)-azetidin-1-yl] pyrazine-2,3-dicarboxamide and N,N’-bis[3,3-dichloro-2-oxo-4-(substitutedpyridine-2-yl)-azetidin-1-yl] pyrazine-2,3-dicarboxamide have been synthesized from the relating newly Schiff bases by [2+2] cycloaddition reaction in good yields. Starting with pyrazine-2,3-dicarboxylic acid which was converted to the corresponding diester in absolute ethanol and glacial acetic acid as a catalyst. After that, the hydazinolysis of resulted diester with hydrazine hydrate afforded dicarbohydrazide which further treated with different substituted pyridine-2-carbaldehyde to give new Schiff bases. These new Schiff bases were reacted with chloroacetochloride and (or) dichloroacetochloride in presence of trimethylamine in DMF solvent under reflux and stirring to yield new derivatives of titled compounds. The structural assignments were estimated from their spectroscopic analysis such as IR,1H NMR, 13C NMR, and C, H, N elemental analysis. The newly prepared 2-azetidinones have been screened for their antimicrobial activity and some of them revealed excellent antibacterial and antifungal activities.
期刊介绍:
Acta Pharmaceutica Sciencia (Acta Pharm. Sci.), formerly known as Bulletin of Pharmacy and Acta Pharmaceutica Turcica is a peer-reviewed scientific journal publishing current research and reviews covering all fields of pharmaceutical sciences since 1953. The original studies accepted for publication must be unpublished work and should contain data that have not been published elsewhere as a whole or a part. The reviews must provide critical evaluation of the state of knowledge related with the subject. All manuscripts has to be written in clear and concise English. Starting from 2016, the journal will be issued quarterly both in paper and on-line formates also publish special issues for national or international scientific meetings and activities in the coverage field.