Synthesis, Fluorescence Properties, and Antiproliferative Potential of Several 3-Oxo-3H-benzo[f]chromene-2-carboxylic Acid Derivatives

Abstract

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.

Sodium ion chemosensor of 3-oxo-3H-benzo[f]chromen-2-carboxylic acid: An experimental and computational study

“…One proton resonance at 9.34 ppm was attributed to an alkene proton of H-14 and other six resonances at 7.59-8.57 ppm were recognized as aromatic naphthalene protons. In addition, 13 different types of carbon appeared in the 13 33 Finally, the molecular formula of 1 was confirmed as C 14 H 8 O 4 by HR-TOF-MS (ESand ES + ) (Fig. S-4.).…”

Novel Synthetic Approach for the Access of Functionalised 4H-Chromenes

“…The desired products 12a 34 addition of the enol form of Meldrum's acid to the keto form of the anil-like compound gives the intermediate 13 followed by loss of amine to form the Knoevenagel-type intermediate 14, which undergoes an intramolecular nucleophilic addition reaction and loss of acetone to afford the product 12a. All of the new compounds were characterised spectroscopically (FTIR, 1 H NMR, 13 C NMR, MS and CHN analyses).…”

Synthesis of alpha-pyrones and chromen-2-ones by transition-metal catalyzed annulations of sulfoxonium and iodonium ylides withcis-stilbene acids

“…Additionally, these ubiquitous structures also offer photophysical properties, especially in the solid state, which have been less explored. 2 The multifarious types of applicability they project inspires the scientific community to develop synthetic approaches for the construction of such relevant frameworks.…”