Synthesis and Characterization of a Multi Ring‐Fused 2‐Pyridone‐Based Fluorescent Scaffold

Abstract

A series of compounds based on a novel fluorescent scaffold have been synthesized. Most of the compounds displayed high quantum yields of fluorescence and unusually long fluorescence lifetimes. HeLa cells were treated with one of the compounds and its use as a fluorescent dye was demonstrated with fluorescence confocal microscopy.

Recent advances in synthesis of 2-pyridones: a key heterocycle is revisited

“…2-Pyridones with fluorescent scaffold have found vast utilities in biology and medicine especially as probes and inhibitors. Sellstedt et al [13] investigated the synthesis of fluorescent compounds with the reaction between acyl Meldrum's acids and thiazoline compounds under microwave irradiation (Scheme 30). Then, compound 97 was obtained by formylation of the product and consequently ring closing under microwave irradiation in the presence of excess TiCl 4 as catalyst which is illustrated in Scheme 31.…”

“…Polyaromatic 2-pyridone systems with their outstanding applications in medicinal chemistry as inhibitor, antibacterial agents, and fluorescent probes had been studied (Scheme 23) [13].…”

“…In recent decades, 2-pyridone and its derivatives have attracted remarkable attention, because of their extensive applications in many fields such as biology [1][2][3][4][5][6][7] natural products [8,9], dyes [10][11][12], and fluorescents [13]. These wide utilities and waves of interest on the 2-pyridone as a key heterocycle, encouraged us to look for the new developments in the synthesis of 2-pyridone in recent years.…”

Microwaves in Heterocyclic Chemistry

“…Under microwave irradiation, reaction times did not exceed 120 s [53]. A novel series of fluorescent 2-pyridinone scaffolds were explored by Almqvist and co-workers [54]. Under microwave irradiation at 125 • C, reaction of Meldrum's acid and thiazoline in 1,2-dichloroethane with TFA (2 equiv.)…”

Synthesis of multi ring-fused imidazo [1,2-a]isoquinoline-based fluorescent scaffold as anti-Herpetic agent

“…For example, it can act as DNA staining dyes, work as intracellular probe or they can also be covalently linked to specific protein to study its mode of action. 14 Diverse synthetic approaches are utilized to synthesize a fused isoquinoline system. The traditional routes such as BischlerÀNapieralski, PictetÀGams, and PomeranzÀFritsch reactions require harsh conditions and highly active substrates.…”