A solvent free, four-component synthesis and 1,3-dipolar cycloaddition of 4(H)-pyrans with nitrile oxides: synthesis and discovery of antimycobacterial activity of enantiomerically pure 1,2,4-oxadiazoles

European Journal of Medicinal Chemistry
Abdulrahman I AlmansourDharmarajan Sriram

Abstract

Four-component reactions of (R)-1-(1-phenylethyl)tetrahydro-4(1H)-pyridinone, aromatic aldehydes and malononitrile in a 1:2:1 molar ratio in the presence of solid sodium ethoxide under solvent free conditions afforded an inseparable mixture of two diastereomeric 4(H)-pyrans in near quantitative yields. These compounds upon 1,3-dipolar cycloaddition with nitrile oxides furnished two enantiomerically pure 1,2,4-oxadiazoles in moderate yields, which were screened for in vitro activity against Mycobacterium tuberculosis H37Rv (MTB) and multi-drug resistant M. tuberculosis (MDR-TB). Among the compounds screened, compound 10h was found to be the most active in vitro with a MIC value of 0.07 and 0.14 μM against MTB and MDR-TB respectively.

References

Dec 1, 2001·Trends in Microbiology·K Höner zu Bentrup, D G Russell
Mar 16, 2002·Science·Christopher DyeMario C Raviglione
Apr 7, 2009·Lancet·Hans L Rieder

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Citations

Aug 7, 2020·Acta Crystallographica. Section C, Structural Chemistry·Svitlana V ShishkinaNatalya D Bunyatyan
Oct 9, 2020·European Journal of Medicinal Chemistry·Santosh Kumar VermaK P Rakesh
Jul 3, 2021·Tuberculosis·Parvinder KaurShridhar Narayanan
Apr 8, 2020·Journal of Medicinal Chemistry·Vadim MakarovSean Ekins

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