Syntheses and biological evaluation of ring-C modified colchicine analogs

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS

卷:20

Article

Yang, Baiyuan¹  Zhu, Zhiqing C.¹  Goodson, Holly V.¹  Miller, Marvin J.¹ 

[1] Univ Notre Dame, Dept Chem & Biochem, Notre Dame, IN 46556 USA

关键词: Colchicine;    Nitroso Diels-Alder;    2-Nitrosopyridine;    Cytotoxicity;    Microtubule;   

DOI  :  10.1016/j.bmcl.2010.03.056

来源: Elsevier

【 摘 要 】

Ring-C modified alkaloids were synthesized from colchicine using iminonitroso Diels-Alder reactions in a highly regio- and stereoselective fashion. Several analogs exhibited cytotoxic activity similar to that of colchicine itself against PC-3 and MCF-7 cancer cell lines, by serving as prodrugs of colchicine through retro Diels-Alder reactions under the assayed conditions. In vitro microtubule polymerization assays indicated that these modifications affected their interaction with tubulin. (C) 2010 Elsevier Ltd. All rights reserved.

【 授权许可】

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