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Coumarin‐Based Bioactive Compounds: Facile Synthesis and Biological Evaluation of Coumarin‐Fused 1,4‐Thiazepines
Author(s) -
Khoobi Mehdi,
Foroumadi Alireza,
Emami Saeed,
Safavi Maliheh,
Dehghan Gholamreza,
Alizadeh Babak H.,
Ramazani Ali,
Ardestani Sussan K.,
Shafiee Abbas
Publication year - 2011
Publication title -
chemical biology and drug design
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.59
H-Index - 77
eISSN - 1747-0285
pISSN - 1747-0277
DOI - 10.1111/j.1747-0285.2011.01175.x
Subject(s) - coumarin , dpph , chemistry , antioxidant , bromide , combinatorial chemistry , mtt assay , ferric , stereochemistry , organic chemistry , biochemistry , in vitro
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.