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Issue 32, 2018
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Synthesis and biological evaluation of cyclic derivatives of combretastatin A-4 containing group 14 elements

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Abstract

Several tricyclic compounds inspired by the structure of combretastatin A-4 and bearing group 14 elements have been synthesized by homocoupling lithiated aryl fragments followed by ring-closing metathesis. These tricyclic compounds and their diolefin precursors were evaluated for their antiproliferative action on the tumor cell lines HT-29, MCF-7, HeLa and A-549 and on the non-tumor cell line HEK-293. In addition, their effects on the cell cycle were also measured. The tricyclic compounds show antiproliferative activity similar to that of combretastatin A-4, even though they are not so active in arresting the cell cycle. However, some diolefin precursors are able to cause accumulation of cells in the G2/M phase in a higher percentage than combretastatin A-4 itself. Inhibition of endothelial tube formation and VEGFR-2 phosphorylation of some selected compounds is comparable to that of combretastatin A-4, particularly those of tin-containing compounds 23c and 26c, whose actions exceed those of sorafenib, a clinically used VEGFR-2 inhibitor.

Graphical abstract: Synthesis and biological evaluation of cyclic derivatives of combretastatin A-4 containing group 14 elements

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Publication details

The article was received on 16 May 2018, accepted on 25 Jul 2018 and first published on 30 Jul 2018


Article type: Paper
DOI: 10.1039/C8OB01148F
Citation: Org. Biomol. Chem., 2018,16, 5859-5870
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    Synthesis and biological evaluation of cyclic derivatives of combretastatin A-4 containing group 14 elements

    V. Blasco, J. Murga, E. Falomir, M. Carda, S. Royo, A. C. Cuñat, J. F. Sanz-Cervera and J. A. Marco, Org. Biomol. Chem., 2018, 16, 5859
    DOI: 10.1039/C8OB01148F

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