کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
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1396739 | 1501197 | 2009 | 9 صفحه PDF | دانلود رایگان |
An efficient synthesis of 1-methyl-3-[(E)-arylmethylidene]tetrahydro-4(1H)-pyridinones was achieved by the reaction of 1-methyl-4-piperidone and aromatic aldehydes in the presence of pyrrolidine under solvent-free microwave irradiation. These dipolarophiles upon cycloaddition with nitrile oxide and azomethine ylides afford stereoselectively novel spiro-isoxazolines, pyrrolizines and pyrrolidines respectively in excellent yields. The spiro compounds were screened for their in vitro activity against Mycobacterium tuberculosis H37Rv (MTB), multi-drug resistant M. tuberculosis (MDR-TB) and Mycobacterium smegmatis (MC2) using agar dilution method. Among the synthesized compounds, 1-methyl-4-(2,4-dichlorophenyl)pyrrolo(spiro[2.3″]oxindole)spiro[3.3′]-1′-methylpiperidin-4′-one was found to be the most active with a minimum inhibitory concentration (MIC) of 1.76 and 0.88 μM against MTB and MDR-TB respectively.
1-Methyl-3-[(E)-arylmethylidene]tetrahydro-4(1H)-pyridinones upon cycloaddition with azomethine ylides afford novel spiro-pyrido-pyrrolizines and pyrrolidines in excellent yields stereoselectively. These spiro-heterocycles exhibit promising in vitro antimycobacterial activity against Mycobacterium tuberculosis.Figure optionsDownload as PowerPoint slide
Journal: European Journal of Medicinal Chemistry - Volume 44, Issue 9, September 2009, Pages 3821–3829