Journal
CHEMICAL BIOLOGY & DRUG DESIGN
Volume 78, Issue 4, Pages 580-586Publisher
WILEY-BLACKWELL
DOI: 10.1111/j.1747-0285.2011.01175.x
Keywords
antioxidant activity; coumarin; cytotoxic activity; phenolic compounds; thiazepine
Funding
- research council of Tehran University of Medical Sciences
- Iran National Science Foundation (INSF)
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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.
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