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. 2017 Jan:117:77-89.
doi: 10.1016/j.steroids.2016.08.002. Epub 2016 Aug 5.

Synthesis of novel lupane triterpenoid-indazolone hybrids with oxime ester linkage

Tatyana S Khlebnicova  1 , Yuri A Piven  1 , Alexander V Baranovsky  1 , Fedor A Lakhvich  1 , Svetlana V Shishkina  2 , Daina Zicāne  3 , Zenta Tetere  3 , Irisa Rāviņa  3 , Viktors Kumpiņš  3 , Inese Rijkure  3 , Inese Mieriņa  3 , Uldis Peipiņš  3 , Māris Turks  4
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Synthesis of novel lupane triterpenoid-indazolone hybrids with oxime ester linkage

Tatyana S Khlebnicova et al. Steroids. 2017 Jan.

Abstract

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: Betulinic acid; Betulonic acid; Indazolone oximes; Triterpenoid-indazolone hybrids; X-ray structure.

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