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Bioorg Med Chem Lett. 2001 Sep 3;11(17):2341-3.

The synthesis and tubulin binding activity of thiophene-based analogues of combretastatin A-4.

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Department of Chemistry, The Faculties, Australian National University, Canberra, ACT 0200, Australia.


A number of analogues of combretastatin A-4 (1), containing a thiophene ring interposed between the two phenyl groups, have been prepared. The synthesis of these compounds employed a combination of palladium-mediated coupling and iodocyclization techniques. The thiophene compounds 11, 14, 18, and 19 also represent non-benzofused analogues of some recently described tubulin binding benzo[b]thiophenes 3-5. The most active thiophene compounds identified in this study were 11, 14, and 18. Overall they are less active than 1 but exhibit comparable activity to the most active of the benzo[b]thiophenes 3-5. A structure-activity relationship of these compounds is considered.

[Indexed for MEDLINE]

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