Synthesis of Novel Lupane Triterpenoid-Indazolone Hybrids with Oxime Ester Linkage

Steroids 2017
Tatyana S. Khlebnicova, Yuri A. Piven, Alexander V. Baranovsky, Fedor A. Lakhvich, Svetlana V. Shishkina, Daina Zicāne, Zenta Tetere, Irisa Rāviņa, Viktors Kumpiņš, Inese Rijkure, Inese Mieriņa, Uldis Peipiņš, Māris Turks

An efficient protocol for the synthesis of novel lupane triterpenoid-indazolone hybrids with oxime ester linkage has been developed from naturally accessible precursor betulin. For the first time a series of betulonic acid-indazolone hybrids have been synthesized via an acylation of corresponding 6,7-dihydro-1H-indazol-4(5H)-one oximes with betulonic acid chloride. Diastereoselective reduction of the obtained betulonic acid conjugates with NaBH4 resulted in a formation of betulinic acid-indazolone hybrids in excellent yields. The configuration of the key compounds has been fully established by X-ray and 2D NMR analysis.

Keywords
Triterpenoid-indazolone hybrids; Betulonic acid; Betulinic acid; Indazolone oximes; X-ray structure
DOI
10.1016/j.steroids.2016.08.002
Hyperlink
http://www.sciencedirect.com/science/article/pii/S0039128X16300988

Khlebnicova, T., Piven, Y., Baranovsky, A., Lakhvich, F., Shishkina, S., Zicāne, D., Tetere, Z., Rāviņa, I., Kumpiņš, V., Rijkure, I., Mieriņa, I., Peipiņš, U., Turks, M. Synthesis of Novel Lupane Triterpenoid-Indazolone Hybrids with Oxime Ester Linkage. Steroids, 2017, Vol.117, pp.77-89. ISSN 0039-128X. e-ISSN 1878-5867. Available from: doi:10.1016/j.steroids.2016.08.002

Publication language
English (en)