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 inRussian chemical bulletin Vol. 65; no. 5; pp. 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 Journal Article
LanguageEnglish
Published New York Springer US 01.05.2016
Springer Nature B.V
Subjects
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Ethylene glycol
Full Articles
Inorganic Chemistry
Organic Chemistry
3-oxobutanoate-containing polyethers
dihydropyrimidine podands
tuberculostatic activity
Biginelli reaction
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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