Fluorescent property of 3-hydroxymethyl imidazo[1,2-a]pyridine and pyrimidine derivatives

Abstract

BackgroundImidazo[1,2-a]pyridines and pyrimidines are important organic fluorophores which have been investigated as biomarkers and photochemical sensors. The effect on the luminescent property by substituents in the heterocycle and phenyl rings, have been studied as well. In this investigation, series of 3-hydroxymethyl imidazo[1,2-a]pyridines and pyrimidines were synthesized and evaluated in relation to fluorescence emission, based upon the hypothesis that the hydroxymethyl group may act as an enhancer of fluorescence intensity.ResultsCompounds of both series emitted light in organic solvents dilutions as well as in acidic and alkaline media. Quantitative fluorescence spectroscopy determined that both fused heterocycles fluoresced more intensely than the parent unsubstituted imidazo[1,2-a]azine fluorophore. In particular, 3-hydroxymethyl imidazo[1,2-a]pyridines fluoresced more intensely than 3-hydroxymethyl imidazo[1,2-a]pyrimidines, the latter emitting blue light at longer wavelengths, whereas the former emitted purple light.ConclusionIt was concluded that in most cases the hydroxymethyl moiety did act as an enhancer of the fluorescence intensity, however, a comparison made with the fluorescence emitted by 2-aryl imidazo[1,2-a]azines revealed that in some cases the hydroxymethyl substituent decreased the fluorescence intensity.

Synthesis, Molecular Docking, and Antimycotic Evaluation of Some 3-Acyl Imidazo[1,2-a]pyrimidines

“…The most widely used method of synthesis for the imidazo[1,2- a ]pyrimidine nucleus was developed by Tschichibabin, based on the reaction between 2-aminopyrimidine and an alpha haloketone [ 23 , 24 , 25 , 26 ]. Despite the fact that imidazo[1,2- a ]pyrimidines have been prepared with diverse variations in methodology, synthesis of 3-benzoyl-substituted imidazo[1,2- a ]pyrimidines without a substituent in position 2 are scarce [ 27 , 28 ].…”

Vegetable Oil-based Hybrid Submicron Particles Loaded with JMV5038: A Promising Formulation against Melanoma

“…For JMV5038, a slight loss was recorded after 190 C highlighting the onset of degradation, followed by a massive loss after 270 C. The residual mass at 600 C was 40.2% of the initial JMV5038 mass, and was consistent with previous studies performed on imidazopyridine (IP) derivatives. 27 Regarding to the ORD, earlier onsets of degradation (i.e. 140 C) and of massive weight loss (i.e.…”

Ionic Liquids-Prompted Synthesis of Biologically Relevant Five- and Six-Membered Heterocyclic Skeletons

“…Besides, imidazo[1,2-a] pyridines and pyrimidines are also attractive due to their physicochemical properties such as fluorescent activity [128]. Indeed, they are known for their anxiolytic, cardiovascular, analgesic, antihypertensive, and neuroleptic among other activities.…”