Synthesis and Cytotoxic Potential of 3-Oxo-19β-trifluoroacetoxy-18α<em>H</em>-oleane-28-oic Acid

Elmira F. Khusnutdinova; Alexander I. Poptsov; Oxana B. Kazakova

doi:10.3390/M1222

Molbank (Jun 2021)

Synthesis and Cytotoxic Potential of 3-Oxo-19β-trifluoroacetoxy-18α<em>H</em>-oleane-28-oic Acid

Elmira F. Khusnutdinova,
Alexander I. Poptsov,
Oxana B. Kazakova

Affiliations

Elmira F. Khusnutdinova: Ufa Institute of Chemistry of the Ufa Federal Research Centre of the Russian Academy of Sciences, 71 pr. Oktyabrya, 450054 Ufa, Russia
Alexander I. Poptsov: Ufa Institute of Chemistry of the Ufa Federal Research Centre of the Russian Academy of Sciences, 71 pr. Oktyabrya, 450054 Ufa, Russia
Oxana B. Kazakova: Ufa Institute of Chemistry of the Ufa Federal Research Centre of the Russian Academy of Sciences, 71 pr. Oktyabrya, 450054 Ufa, Russia

DOI: https://doi.org/10.3390/M1222
Journal volume & issue: Vol. 2021, no. 2
p. M1222

Abstract

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Trifluoroacetic acid-promoted Wagner-Meerwein rearrangement of betulonic acid carboxamide led to the formation of the expected 19β,28-lactam along with a new germanicane-type 3-oxo-19β-trifluoroacetoxy-18αH-oleane-28-oic acid. The structure of this triterpenoid was confirmed by 2D NMR analyses. A primary evaluation of biological potency revealed an anticancer activity with GI50 < 5 μM against leukemia, colon cancer, breast cancer, and prostate cancer cell lines, while the parent compounds were not active.

Published in Molbank

ISSN: 1422-8599 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Inorganic chemistry
Website: https://www.mdpi.com/journal/molbank

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