Novel cyanocombretastatins as potent tubulin polymerisation inhibitors

Novel cyanocombretastatins as potent tubulin polymerisation inhibitors

A series of novel cyanocombretastatins bearing a 3,4,5-trimethoxyphenyl moiety combined with a variety of substituted phenyl rings, were synthesised and their antitumour activity was evaluated. The Z-cyanocombretastatins were synthesised in a one-step protocol in high purity and yield. Fluoro, bromo...

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Veröffentlicht in:Bioorganic & medicinal chemistry letters 2012-11, Vol.22 (21), p.6731-6734
Hauptverfasser: Jalily, Pouria H., Hadfield, John A., Hirst, Nicholas, Rossington, Steven B.
Format: Artikel
Sprache:eng
Schlagworte:
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Antiproliferative activity
Bibenzyls - chemical synthesis
Bibenzyls - chemistry
Bibenzyls - pharmacology
Biological and medical sciences
CA-4 analogues
Cell Line, Tumor
Cell Proliferation - drug effects
Combretastatins
Cyanocombretastatins
Humans
Indexing in process
Inhibitory Concentration 50
Magnetic Resonance Spectroscopy
Medical sciences
Molecular Structure
Nitriles - chemical synthesis
Nitriles - chemistry
Nitriles - pharmacology
Pharmacology. Drug treatments
Tubulin Modulators - chemical synthesis
Tubulin Modulators - chemistry
Tubulin Modulators - pharmacology
Tubulin polymerisation inhibitor
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Zusammenfassung:A series of novel cyanocombretastatins bearing a 3,4,5-trimethoxyphenyl moiety combined with a variety of substituted phenyl rings, were synthesised and their antitumour activity was evaluated. The Z-cyanocombretastatins were synthesised in a one-step protocol in high purity and yield. Fluoro, bromo, iodo, and derivatives with boronic acid and an ethyne function at meta position of the B ring were synthesised. In vitro MTT bioassays against human chronic myelogenous leukaemia (K562) and transfected breast adenocarcinoma (MDA NQO1) cell lines, revealed promising IC50 inhibitory values in nanomolar range (
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2012.08.089