Synthesis and tuberculostatic activity of podands with a dihydropyrimidine fragment

A method for the preparation of 3-oxobutanoate-containing podands differing in the length of the polyether fragment by acetoacetylation of oligo(ethylene glycols) with 2,2,6-trimethyl-4 H -1,3-dioxin-4-one upon heating in toluene was optimized. A multi-component Biginelli reaction was used for the f...

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Bibliographic Details
Published in:Russian chemical bulletin 2016-05, Vol.65 (5), p.1360-1364
Main Authors: Filatova, E. S., Fedorova, O. V., Titova, Yu. A., Slepukhin, P. A., Kravchenko, M. A., Skornyakov, S. N., Rusinov, G. L., Charushin, V. N.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Dioxins
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Inorganic Chemistry
Organic Chemistry
Toluene
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Summary:A method for the preparation of 3-oxobutanoate-containing podands differing in the length of the polyether fragment by acetoacetylation of oligo(ethylene glycols) with 2,2,6-trimethyl-4 H -1,3-dioxin-4-one upon heating in toluene was optimized. A multi-component Biginelli reaction was used for the formation of the dihydropyrimidine ring on the ether matrix obtained. Tuberculostatic activity of dihydropyrimidine podands in the in vitro experiments against a laboratory strain H 37 Rv was studied. A combination of dihydropyrimidine and podand fragments imparts tuberculostatic activity to the compounds obtained, which noticeably enhances with the increase in the oxyethylene spacer length.
ISSN:1066-5285
1573-9171
DOI:10.1007/s11172-016-1462-4