Divergent synthesis and antitumour activity of novel conformationally constrained (–)-muricatacin analogues Scientific paper

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Slađana M. Stanisavljević
Bojana Srećo Zelenović
Mirjana Popsavin
Marko V. Rodić
Velimir Popsavin
Vesna V. Kojić


Four novel conformationally restricted (–)-muricatacin analogues, bearing a methoxy group at the C-5 position and with an alkoxymethyl group аs the C-7 side chain, have been synthesised and their in vitro antiproliferative activity was evaluated against a panel of seven human tumour cell lines, as well as a single normal cell line. All analogues (912) showed diverse anti­pro­liferative effects against all tested human malignant cell lines, but were devoid of any significant cytotoxicity towards the normal foetal lung fibroblasts (MRC-5). A structure–activity relationship study reveals that the introduction of tetrahydrofuran ring, the replacement of C-8 methylene group in the side chain of muricatacin analogues with the O-8 ether functionality, as well as the length of side chain may be beneficial for the antiproliferative effects of these lactones. All novel analogues were more potent than lead compound, (–)-muri­catacin, against HL-60 cell line.


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S. Stanisavljević, B. Srećo Zelenović, M. Popsavin, M. Rodić, V. Popsavin, and V. Kojić, “Divergent synthesis and antitumour activity of novel conformationally constrained (–)-muricatacin analogues: Scientific paper”, J. Serb. Chem. Soc., vol. 88, no. 2, pp. 113–121, Nov. 2022.
Organic Chemistry

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