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Synthesis, biology, and modeling of a C-4 carbonyl C,D-seco-taxoid |
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| Authors: | Zorana Ferjancic Radomir Matovic Yi Jiang Vladimir Trajkovic |
| Institution: | a Faculty of Chemistry, University of Belgrade, Studentski trg 16, PO Box 158, 11000 Belgrade, Serbia and Montenegro b ICTM, Center for Chemistry, Njegoševa 12, 11000 Belgrade, Serbia and Montenegro c Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, GA 30322, USA d School of Medicine, University of Belgrade, Dr Subotica 1, 11000 Belgrade, Serbia and Montenegro |
| Abstract: | A C,D-seco-paclitaxel derivative 26 was prepared from taxine and tested for biological activity. Chemical reactivity of the seco-compounds proved to be substantially modified, with respects to taxoids. The corresponding C,D-seco-taxoid does not show tubulin stabilizing activity or cytotoxicity. Explanation of these observations based on molecular modeling is provided. |
| Keywords: | Taxane antitumor agents Radicals and radical reactions Medium sized rings Natural products Molecular modeling |
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