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二茂铁基吲哚啉酮的合成、电化学研究及抗癌活性

Synthesis, electrochemical studies and anticancer activity of ferrocenyl oxindoles.

机构信息

Instituto de Química-CT, Bloco A, Universidade Federal do Rio de Janeiro, Cidade Universitária, 21945-970, Rio de Janeiro, RJ, Brazil.

出版信息

Dalton Trans. 2010 Aug 21;39(31):7338-44. doi: 10.1039/c002983a. Epub 2010 Jul 2.

Abstract

A series of (E) and (Z)-ferrocenyl oxindoles were prepared by coupling substituted oxindoles to ferrocenylcarboxyaldehyde in the presence of morpholine as a catalyst. The redox behavior of these isomers was determined by cyclic voltammetry. The effects of the oxindole derivatives on the migration of human breast cancer cells were evaluated using the wound-healing assay and the Boyden chamber cell-migration assay. The most potent Z isomers 11b (IC(50) = 0.89 microM), 12b (IC(50) = 0.49 microM) and 17b (IC(50) = 0.64 microM) could represent attractive new lead compounds for further development for cancer therapy.

摘要

(E)和(Z)-二茂铁基氧吲哚类化合物的合成,是在吗啉作为催化剂的条件下,取代的氧吲哚与二茂铁基甲醛缩合得到的。通过循环伏安法测定了这些异构体的氧化还原行为。采用划痕实验和 Boyden 室细胞迁移实验评价了氧吲哚衍生物对人乳腺癌细胞迁移的影响。最有效的 Z 异构体 11b(IC50 = 0.89 μM)、12b(IC50 = 0.49 μM)和 17b(IC50 = 0.64 μM)可能代表有吸引力的新先导化合物,可进一步开发用于癌症治疗。

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