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

Chemistry of Natural Compounds 2022
M.D. Semenova, S.A. Popov, E.E. Shul`ts, Māris Turks

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.

Keywords
1,2,4-triazole-5(4H)-thione | 1,3,4-oxadiazole-2(3H)-thione | 2-(methanesulfonyl)-1,3,4-oxadiazole | Mannich reaction | nucleophilic substitution | ursolic acid
DOI
10.1007/s10600-022-03597-x
Hyperlink
https://link.springer.com/article/10.1007/s10600-022-03597-x

Semenova, M., Popov, S., Shul`ts, E., Turks, M. Synthesis of New Ursane-Type Hybrids with Morpholinomethyl-, Dialkylamino-, and Hydroxyl-Substituted Azoles. Chemistry of Natural Compounds, 2022, Vol. 58, No. 1, pp.65-70. ISSN 0009-3130. Available from: doi:10.1007/s10600-022-03597-x

Publication language
English (en)