Synthesis and Antioxidant Activity of New N-Containing Hybrid Derivatives of Gallic and Ursolic Acids

Chemistry of Natural Compounds 2021
S.A Popov, C Wang, Z Qi, E.E Shults, Māris Turks

New hybrid derivatives of ursolic and gallic acids linked through an ethylene linker and containing hydrazide and 1,3,4-oxadiazol-2-thione as terminal substituents were synthesized. Hydrazinolysis of methyl 3-(3β-acetoxyurs-12-en-28-oyloxy)-4,5-dihydroxybenzoate led to cleavage at the triterpenoid C-28-ester bond to produce (3β-acetoxyurs-12-en)-28-oyl hydrazide and methyl gallate. The dioxolane protecting group on the polyphenol moiety was easily removed with retention of the ester on the aromatic moiety during the reaction of hydrazine with methyl 3-(3β-acetoxyurs-12-en-28-oyloxy)-4,5-[(R,S)-methoxymethylenedioxy]benzoate. The new hybrid derivatives of ursolic and gallic acids containing hydrazide and 1,3,4-oxadiazole moieties possessed high antioxidant activity.

Keywords
1,3,4-oxadiazole | antioxidant activity | gallic acid | hybrid derivatives | hydrazide | hydrazinolysis | ursolic acid
DOI
10.1007/s10600-021-03546-0
Hyperlink
https://link.springer.com/article/10.1007%2Fs10600-021-03546-0

Popov, S., Wang, C., Qi, Z., Shults, E., Turks, M. Synthesis and Antioxidant Activity of New N-Containing Hybrid Derivatives of Gallic and Ursolic Acids. Chemistry of Natural Compounds, 2021, Vol. 57, No. 6, pp.1042-1046. ISSN 0009-3130. e-ISSN 1573-8388. Available from: doi:10.1007/s10600-021-03546-0

Publication language
English (en)