Abstract
In this study, two series of 3-oxo-3H-benzo[f]chromene-2-carboxylic acid derivatives (compounds 5a–i and 6a–g) were synthesized. Their in vitro proliferation inhibitory activities against the A549 and NCI-H460 human non-small cell lung cancer (NSCLC) cell lines were evaluated. Their photophysical properties were measured. Among these target compounds, 5e exhibited the strongest antiproliferative activity by inducing apoptosis, arresting cell cycle, and elevating intracellular reactive oxygen species (ROS) level, suggesting that it may be a potent antitumor agent. In addition, compound 6g with very low cytotoxicity, demonstrated excellent fluorescence properties, which could be used as an effective fluorescence probe for biological imaging.
Highlights
Coumarin (1,2-benzopyrone or 2H-1-benzopyran-2-one) and its derivatives, best-known as oxygen-containing heterocyclic compounds, are widely distributed in Nature and many exhibit diverse biological and interesting pharmacological activities
It was found that compound 5e exhibited the strongest in vitro proliferation inhibitory activity against the A549 and NCI-H460 cell lines, suggesting that it may be a potent antitumor agent
The in vitro proliferation inhibitory activity of the prepared compounds 5a–i and 6a–g was evaluated against two non-small cell lung cancer (NSCLC) cell lines including A549 and NCI-H460; 7-hydroxycoumarin (7-HC) and cisplatin were selected as dual positive reference drugs
Summary
Coumarin (1,2-benzopyrone or 2H-1-benzopyran-2-one) and its derivatives, best-known as oxygen-containing heterocyclic compounds, are widely distributed in Nature and many exhibit diverse biological and interesting pharmacological activities. The excellent fluorescent properties of coumarin compounds offer additional development value and they are used in many areas, such as fluorescent brighteners, fluorescent probes to monitor complex biological events, electroluminescent devices, photochemotherapy, etc. Two series of 3-oxo-3H-benzo[f]chromene-2-carboxylic acid derivatives including its amide (compounds 5a–i) and ester (compounds 6a–g) were efficiently synthesized (Scheme 1). Their biological activity and photophysical properties were evaluated. Compound 6g with very low cytotoxicity demonstrated excellent fluorescence properties, which could be exploited for biological and biomedical imaging. Synthetic route to the target compounds 3-oxo-3H-benzo[f]chromene-2-carboxylic acid derivatives 5a–i and 6a–g. Reagents and conditions: (a) Meldrum’s acid (2), ethanol, pyridine, 80 °C, 4 h; (b) SOCl2, 1,2-dichloroethane, 60–70 °C, 4 h; (c) R1-NH2, triethylamine, CH2Cl2, room temperature (r.t.), 10–30 min; (d) R2-OH, triethylamine, CH2Cl2, r.t., 10–30 min
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