Synthesis and biological evaluation of novel heterocyclic derivatives of combretastatin A-4

The preparation and biological evaluation of new 3,4,5-trimethoxy styrene heterocylic derivatives are described. A novel series of combretastatin A-4 heterocyclic analogues was prepared by replacement of the B ring with indole, benzofurane or benzothiophene, attached at the C2 position. These compou...

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Veröffentlicht in:	Bioorganic & medicinal chemistry letters 2012-12, Vol.22 (23), p.7227-7231
Hauptverfasser:	Nguyen, Thi Thanh Binh, Lomberget, Thierry, Tran, Ngoc Chau, Colomb, Evelyne, Nachtergaele, Lore, Thoret, Sylviane, Dubois, Joëlle, Guillaume, Joren, Abdayem, Rawad, Haftek, Marek, Barret, Roland
Format:	Artikel
Sprache:	eng
Schlagworte:	Antimitotic Antimitotic Agents - chemical synthesis Antimitotic Agents - chemistry Antimitotic Agents - toxicity Benzofurans - chemistry Benzoheterocycles Biological and medical sciences Cancer Cell Cycle Checkpoints - drug effects Cell Line, Tumor Cell Proliferation - drug effects Chemical Sciences Colchicine Colchicine - pharmacology Combretastatin A-4 Confocal microscopy Heterocyclic Compounds - chemistry Humans Indole Indoles - chemistry Inhibitors of tubulin assembly Keratinocyte Keratinocytes Medical sciences microscopy Microscopy, Confocal Microtubules Microtubules - chemistry Microtubules - metabolism Organic chemistry Pharmacology. Drug treatments Stereoisomerism Stereoisomers Stilbenes - chemical synthesis Stilbenes - chemistry Stilbenes - toxicity Thiophenes - chemistry Tubulin Tumor cell lines
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Zusammenfassung:	The preparation and biological evaluation of new 3,4,5-trimethoxy styrene heterocylic derivatives are described. A novel series of combretastatin A-4 heterocyclic analogues was prepared by replacement of the B ring with indole, benzofurane or benzothiophene, attached at the C2 position. These compounds were evaluated for their abilities to inhibit tubulin assembly: derivative cis3b, having a benzothiophene, showed an activity similar to those of colchicine or deoxypodophyllotoxine. The antiproliferative and antimitotic properties of cis3b against keratinocyte cancer cell lines were also evaluated and the intracellular organization of microtubules in the cells after treatment with both stereoisomers of 3b was also determined, using confocal microscopy.
ISSN:	0960-894X 1464-3405
DOI:	10.1016/j.bmcl.2012.09.047