Synthesis of hybrid compounds of 24-nor-lupane triterpene and amino acids via C-28 amide linkage
Keywords
DOI:
https://doi.org/10.26459/hueunijns.v132i1B.6810Abstract
Betulinic acid derivatives exhibit different biological activity against diversified targets, such as anticarcinogenic activity in experimental animals, anti-HIV, antihyperglycemia, and anti-inflammatory in humans. In this work, we investigated the synthetic procedure of 24-nor-3-oxo-20(29)-lupen-28-oic acid (1) derivatives. Starting from compound 1 and L-leucine methyl ester, we proceeded with amidification, reduction, and hydrolysis under basic conditions. Finally, three hybrid compounds were successfully synthesised and elucidated with spectral means.Downloads
References
1. Khlebnicova TS, Piven YA, Baranovsky AV, Lakhvich FA, Sorokina IV, Tolstikova TG. Fluorine-containing lupane triterpenoid acid derivatives: Design, synthesis and biological evaluation as potential anti-inflammatory agents, Steroids. 2019;147:62-69.
2. Giang LNT, Nga NT, Hai PT, Anh DTT, Huong NT, Ha NTT, et al. Synthesis and biological evaluation of novel quinazoline-triazole hybrid compounds with potential use in Alzheimer’s disease. Bioorganic & Medicinal Chemistry Letters. 2020;30(18):127404.
3. Jäger S, Trojan H, Kopp T, Laszczyk MN, Scheffler A. Pentacyclic triterpene distribution in various plants – rich sources for a new group of multi-potent plant extracts. Molecules. 2009;14:2016-2031.
4. Shin J, Lee HJ, Jung DB, Jung JH, Lee HJ, Lee EO, et al. Suppression of STAT3 and HIF-1 alpha mediates anti-angiogenic activity of betulinic acid in hypoxic PC-3 prostate cancer cells. PLoS One. 6(6):e21492,.
5. Dehelean CA, Feflea S, Ganta S, Amiji M. Antiangiogenic effects of betulinic acid administered in nanoemulsion formulation using chorioallantoic membrane assay, Journal of Biomedical Nanotechnology. 2011;7(2):317-324.
6. Anh DTT, Cuc DT, Giang LNT, Hien NT, Doan VN, Thanh NT, et al. Design, synthesis and cytotoxic evaluation of novel lupane triterpenoid and ursolic acid derived 2-aminobenzamides. Natural Product Communications. 2018;13(7):817-822.
7. Tam NT, Nhung LTH, Thien DD, Chien TV, Sung TV. Synthesis and cytotoxic activity of derivatives of 24-nor-lupane-triterpenoid acids isolated from Acanthopanax trifoliatus. Chemistry of Natural Compounds. 2015;51(2):276-282,
8. Kim DSHL, Chen Z, Tuyen NV, Pezzuto JM, Qiu S, Lu ZZ. A concise semi-synthetic approach to betulinic acid from betulin. Synthetic Communications. 1997;27(9):1607-1612.
