Coumarin-Based Bioactive Compounds: Facile Synthesis and Biological Evaluation of Coumarin-Fused 1,4-Thiazepines

Mehdi Khoobi; Alireza Foroumadi; Saeed Emami; Maliheh Safavi; Gholamreza Dehghan; Babak H. Alizadeh; Ali Ramazani; Sussan K. Ardestani; Abbas Shafiee

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Coumarin-Based Bioactive Compounds: Facile Synthesis and Biological Evaluation of Coumarin-Fused 1,4-Thiazepines

机译：基于香豆素的生物活性化合物：香豆素融合的1,4-硫氮平的简便合成和生物学评估

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As part of our ongoing studies on the synthesis of bioactive coumarin compounds, we synthesized a series of new coumarin-fused 1,4-thiazepines using a simple method. The biological activity of target compounds along with 3-(2-hydroxybenzylidene) chroman-2,4-dione intermediates was screened by evaluation of their antioxidant and cytotoxic activities. The antioxidant activity was assessed using two methods, namely, 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging method and ferric reducing antioxidant power (FRAP) assay. 4- Methoxyphenolic compound 5d in thiazepine series showed the most potent scavenging activity, while the 4-bromophenolic derivative 5b was the most efficient compound in FRAP assay. Also, the result of cytotoxic evaluation using MTT [3-(4,5- dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide] assay demonstrated that compound 5b is at least twofold more potent than etoposide against MCF-7, SK-N-MC, and MDA-MB 231 cell lines.

机译：作为我们正在进行的有关合成生物活性香豆素化合物的研究的一部分，我们使用一种简单的方法合成了一系列新的香豆素融合的1,4-噻氮平。通过评价抗氧化剂和细胞毒性活性，筛选了目标化合物与3-（2-羟基苄叉基）苯并二氢吡喃-2-，4-二酮中间体的生物活性。使用两种方法评估抗氧化活性，即1,1-二苯基-2-吡啶并肼基（DPPH）自由基清除法和还原铁抗氧化能力（FRAP）分析。噻氮平系列中的4-甲氧基酚化合物5d表现出最强的清除活性，而4-溴酚衍生物5b是FRAP分析中最有效的化合物。同样，使用MTT [3-（4,5-二甲基噻唑-2-基）-2,5-二苯基溴化四唑鎓]细胞毒性评估的结果表明，化合物5b对依托泊苷的抗药性至少比对依托泊苷高两倍， SK-N-MC和MDA-MB 231细胞系。

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《Chemical biology and drug design》 |2011年第4期|共7页
作者
Mehdi Khoobi; Alireza Foroumadi; Saeed Emami; Maliheh Safavi; Gholamreza Dehghan; Babak H. Alizadeh; Ali Ramazani; Sussan K. Ardestani; Abbas Shafiee;
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正文语种 eng
中图分类化学药理学;
关键词
antioxidant activity; coumarin; cytotoxic activity; phenolic compounds; thiazepine;

机译：抗氧化剂活性;香豆素;细胞毒活性;酚类化合物;硫氮平;

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1. Coumarin-Based Bioactive Compounds: Facile Synthesis and Biological Evaluation of Coumarin-Fused 1,4-Thiazepines [J] . Mehdi Khoobi, Alireza Foroumadi, Saeed Emami, Chemical biology and drug design . 2011,第4期

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Coumarin-Based Bioactive Compounds: Facile Synthesis and Biological Evaluation of Coumarin-Fused 1,4-Thiazepines

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