Synthesis of 4‐Hydroxy‐2‐pyridinone Derivatives and Evaluation of Their Antioxidant/Anticancer Activities

Abstract

A simple approach was applied for the regioselective synthesis of various pyridine‐2‐one derivatives or annulated pyridine as novel heterocyclic systems from the reaction of dehydroacetic acid (DHA) with mono‐ or bidentate nucleophile as with benzylamine and/or phenylenediamines in dichloromethane followed by transformation with different halo‐compounds in refluxing 1,4‐dioxane has been achieved in moderate to excellent yields (48‐93 %). In addition, DFT studies of the key synthesized compounds were carried out for confirmed proposed mechanisms. The newly synthesized compounds were screened for their in‐vitro inhibition activities against mammary gland breast cancer (MCF‐7) and human prostate cancer (PC‐3) using the MTT colorimetric method. Also, the target synthesized compounds were evaluated as antioxidant agents.

Efficient Synthesis of Bicyclic 2‐Pyridinones and 6‐Amino‐2‐pyridinones by the Regioselective Cycloaddition of Nitro Ketene Aminal with 3‐Hydroxy‐2‐aryl‐acrylate

“…Optimization for the synthesis of bicyclic 2-pyridinones 3 a. [a] Entry Solvent Promoter Compounds 3 and 4 were fully characterized by 1 H NMR, 13 C NMR, IR spectroscopy, and high-resolution mass spectrometry (see the Supporting Information). To further characterize the bicyclic 2-pyridinones and monocyclic 2-pyridinones, the crystal structures of representative compounds 3 a (CCDC 2183992) and 4 n (CCDC 2183993) were determined by X-ray crystallographic analysis (Figure 4).…”

“…[12] Thus, studies of 2-pyridinones can help achieve better drug-like properties, and the efficient and benign synthesis of diverse functionalized 2-pyridinones has recently attracted significant attention. [13,14] Among 2-pyridinone derivatives, multi-substituted bicyclic 2-pyridinones are ring-fused compounds with complex structures. They have been found in a wide range of natural products [15][16][17] and have shown interesting medicinal properties, such as antitumor (A58365B), pilus inhibitors (FN075), and kinase inhibitors (Duvelisib) (Figure 1).…”

Enhanced performance of hydroxyl and cyano group functionalized graphitic carbon nitride for efficient removal of crystal violet and methylene blue from wastewater

“…Theoretical studies were applied through using density functional theory (DFT) of Gaussian 09 program package in the presence of a combination level of 6-311G (d to p) and (B3LYP) as exchange function for these computations to elucidate the adsorption mechanism of CV and MB dyes from wastewater at electronic scale on the basis of their expected quantum calculations. 4,30–32…”

A Comparative DFT Study on the Antioxidant Activity of Some Novel 3‐Hydroxypyridine‐4‐One Derivatives

“…Aromaticity increases its OH group acidity and allows it to show phenolic properties [41] . Due to this characteristic hydroxypyrones and hydroxypyridinones can act as good radical scavengers [42] …”

“…[41] Due to this characteristic hydroxypyrones and hydroxypyridinones can act as good radical scavengers. [42] Aromaticity is a property that can influence the antioxidant properties of studied compounds. The core of the tested compounds are their heterocyclic units.…”