Microwave-assisted synthesis of sec/tert-butyl 2-arylbenzimidazoles and their unexpected antiproliferative activity towards ER negative breast cancer cells
Microwave-assisted synthesis of sec/tert-butyl 2-arylbenzimidazoles and their unexpected antiproliferative activity towards ER negative breast cancer cells
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DOI：
10.3109/14756366.2012.729828
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发表时间：
2013-12-01
影响因子：
5.6
通讯作者：
Mat, Ishak B.
中科院分区：
文献类型：
--
作者：
Rahim, Aisyah Saad Abdul;Salhimi, Salizawati Muhamad;Mat, Ishak B.
通过在聚焦微波辐射下，3-氨基-4-丁基氨基苯甲酸乙酯与苯甲醛的各种取代焦亚硫酸盐加合物缩合，在2-3.5分钟内合成了一系列新的N-仲/叔丁基2-芳基苯并咪唑衍生物，收率85-96%。使用 H-1 NMR、C-13 NMR、高分辨率 MS 和熔点对苯并咪唑类似物进行了表征。对苯并咪唑类似物针对 MCF-7 和 MDA-MB-231 的抗增殖活性的评估揭示了几种化合物在微摩尔范围内对 MDA-MB-231 具有意想不到的选择性抑制作用。发现所有类似物对 MCF-7 均无活性。对 MDA-MB-231 人乳腺癌细胞系最有效的抑制来自未取代的 2-苯基苯并咪唑 10a。
A new series of N-sec/tert-butyl 2-arylbenzimidazole derivatives was synthesised in 85-96% yields within 2-3.5 min by condensing ethyl 3-amino-4-butylamino benzoate with various substituted metabisulfite adducts of benzaldehyde under focused microwave irradiation. The benzimidazole analogues were characterised using H-1 NMR, C-13 NMR, high resolution MS and melting points. Evaluation of antiproliferative activity of the benzimidazole analogues against MCF-7 and MDA-MB-231 revealed several compounds with unexpected selective inhibitions of MDA-MB-231 in micromolar range. All analogues were found inactive towards MCF-7. The most potent inhibition against MDA-MB-231 human breast cancer cell line came from the unsubstituted 2-phenylbenzimidazole 10a.