3,28-Bis-<Emphasis Type="Italic">O</Emphasis>-polyfluorobenzoylbetulin. Synthesis,Molecular Structure,and Cytotoxicity |
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| Authors: | Yu G Trishin A N Fedorov K A Lyssenko D S Prokof’eva Yu S Rudenok V V Pavlova |
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| Institution: | 1.Higher School of Technology and Energy,St. Petersburg State University of Industrial Technologies and Design,St. Petersburg,Russia;2.Nesmeyanov Institute of Organoelement Compounds,Russian Academy of Sciences,Moscow,Russia;3.Institute of Experimental Pharmacology,Kuz’molovskii, Leningrad oblast,Russia |
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| Abstract: | Treatment of betulin with 2,3,4,5-tetrafluoro- and pentafluorobenzoyl chlorides in triethylamine afforded 3,28-bis-O-polyfluorobenzoylbetulins. According to the X-ray diffraction data, all six-membered rings in the 3,28-bis-O-pentafluorobenzoylbetulin molecule appear in a chair conformation, and the five-membered ring has an envelope conformation with the C17 atom deviating from the plane formed by the other four carbon atoms. Unlike betulin itself, the obtained bis-esters showed no cytotoxic effect on human lung adenocarcinoma cell line A549 and human glioblastoma cell line U251. |
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