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

Abstract

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.

Synthesis of Methoxy‐substituted Chalcones and in vitro Evaluation of their Anticancer Potential

“…If there are solubility problems, DMSO was found to be an appropriate solvent to dissolve the crystals of formazan . However, in our study, we followed the original method of Mosmann, and the solvent used was isopropyl alcohol, and a wave length of 570 nm was utilized as reported …”

Coumarin heterocyclic derivatives: chemical synthesis and biological activity

“…212 Thus, 4-hydroxycoumarin derivatives 26 were converted to the corresponding benzylidene derivatives 294-295. Reaction of 2-aminoethanethiol hydrochloride with benzylidene derivative 295 gave the corresponding fused heterocycle 296.…”

Synthesis of Novel 4H-Chromenes Containing a Pyrimidine-2-Thione Function in the Presence of Fe3O4 Magnetic Nanoparticles and Study of Their Antioxidant Activity

“…Water is an obviously benign and inexpensive solvent to reduce pollution, cost, and tedious work-ups in synthetic methodologies. Bearing in mind the usefulness and efficiency of Fe 3 O 4 NPs in organic reactions 22 and in connection with our previous works on evaluation of biological active compounds, 23,24 we decided to explore an application of Fe 3 O 4 NPs for the preparation of 2-amino-4-aryl-4H-chromene-3-carbonitrile derivatives 5 with using multicomponent reaction 25 of 1, 2, and 4 (Scheme 1). Also, a novel series of chromenopyrimidinethione derivatives 8 were synthesized in order to develop novel antioxidant agents with low cytotoxicity activity.…”