Structural requirements for the binding of colchicine analogs to tubulin: the role of the C-10 substituent

Derivatives of colchicine and the bicyclic colchicine analog 2-methoxy-5-(2',3',4'-trimethoxyphenyl)tropone were tested for inhibition of tubulin polymerization. The nature of the tropone substituent had litte effect on the efficacy of the colchicine series, with some exceptions. In c...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 1991, Vol.1 (9), p.471-476
Main Authors: Hahn, Klaus M., Humphreys, W.Griffith, Helms, Anna M., Hastie, Susan Bane, Macdonald, Timonthy L.
Format: Article
Language:English
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Summary:Derivatives of colchicine and the bicyclic colchicine analog 2-methoxy-5-(2',3',4'-trimethoxyphenyl)tropone were tested for inhibition of tubulin polymerization. The nature of the tropone substituent had litte effect on the efficacy of the colchicine series, with some exceptions. In contrast, the potency of the bicyclic analogs varied greatly with the tropone substituent. Derivatives of colchicine ( I) and its bicyclic analog ( II) with varying tropone substituents (R) were prepared and assayed for inhibition of microtubule assembly. Significantly greater variations in potency are observed in the bicyclic series than in the colchicine series.
ISSN:0960-894X
1464-3405
DOI:10.1016/S0960-894X(01)81108-2