Abstract
Betulin derivatives are a widely studied group of compounds of natural origin due to their wide spectrum of biological activities. This paper describes new betulin derivatives, containing a phosphonate group. The allyl-vinyl isomerization and synthesis of acetylenic derivatives have been reported. Structural identification of products as E and Z isomers has been carried out using 1H-, 13C-, 31P-NMR, and crystallographic analysis. The crystal structure in the orthorhombic space group and analysis of crystal packing contacts for 29-diethoxyphosphoryl-28-cyclopropylpropynoyloxy-lup-20E(29)-en-3β-ol 8a are reported. All new compounds were tested in vitro for their antiproliferative activity against human T47D (breast cancer), SNB-19 (glioblastoma), and C32 (melanoma) cell lines.
Highlights
Natural plant products are an important source of the exploration and development of new anticancer drugs
As an extension of our study on the development of novel betulin derivatives with potential anticancer activity, we became interested in the synthesis and evaluation of cytotoxicity of betulins containing a phosphonate group at the C30 position
The synthesis of the phosphonate waswork carried insynthesized good out yield
Summary
Natural plant products are an important source of the exploration and development of new anticancer drugs. 1 in white birch bark (up to 30%) and the presence of two hydroxyl groups at C3 and C28 and an isopropenyl group at C19 results in compound 1 being a good material for the preparation of new derivatives with a broad spectrum of biological activities, such as anticancer, antiviral, antimalarial, antibacterial, anti-inflammatory, and hepatoprotective [1]. It was reported that the introduction of substituents containing a triple bond into the betulin 1 results in derivatives with increased cytotoxicity, and provides a starting point for further modification of the compound [2,3,4]. As an extension of our study on the development of novel betulin derivatives with potential anticancer activity, we became interested in the synthesis and evaluation of cytotoxicity of betulins containing a phosphonate group at the C30 position. Among phosphonates, one can find active substances such as antiviral, antibacterial, antitumor, and Molecules 2016, 21, 1123; doi:10.3390/molecules21091123 www.mdpi.com/journal/molecules
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