Synthesis of New Ursane-Type Hybrids with Morpholinomethyl-, Dialkylamino-, and Hydroxyl-Substituted Azoles

Ursane-type triterpenoids containing functionalized heterocyclic substituents were chemically modified. Aminomethylation of ursane hybrids with 1,3,4-oxadiazole- and 1,2,4-triazolethiones occurred smoothly to form new potentially biologically active derivatives of pentacyclic triterpenoids containin...

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Bibliographic Details
Published in:Chemistry of natural compounds 2022, Vol.58 (1), p.65-70
Main Authors: Semenova, M. D., Popov, S. A., Shul’ts, E. E., Turks, M.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Heterocyclic compounds
Hydroxides
Organic Chemistry
Oxadiazoles
Plant Sciences
Triazoles
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Summary:Ursane-type triterpenoids containing functionalized heterocyclic substituents were chemically modified. Aminomethylation of ursane hybrids with 1,3,4-oxadiazole- and 1,2,4-triazolethiones occurred smoothly to form new potentially biologically active derivatives of pentacyclic triterpenoids containing 4-morphlinomethyl-5-thioxo-1,3,4-oxadiazole or 4-morpholinomethyl-5-thioxo-1,2,4-triazole substituents. Nucleophilic substitution of a methanesulfonyl group in a 1,3,4-oxadiazole substituent of a pentacyclic triterpenoid synthesized ursane-type hybrids with 2-hydroxyoxadiazoles and 2-dialkylaminooxadiazoles.
ISSN:0009-3130
1573-8388
DOI:10.1007/s10600-022-03597-x