Crystal structure of 2-(4-methoxyphenyl)-6-nitroimidazo[1,2-<i>a</i>]pyridine-3-carbaldehyde

Koudad, Mohamed; Elaatiaoui, A.; Benchat, N.; Saadi, Mohamed; Ammari, Lahcen El

doi:10.1107/s2056989015021957

Cited by 4 publications

(3 citation statements)

References 16 publications

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“…7d). (Nair et al, 2012) ethyl (imidazo[1,2-a]pyridin-3-yl)acetate phenyl 38.6 DABTEI (Koudad et al, 2015) 6-nitroimidazo[1,2-a]pyridinyl-3-carbaldehyde 4-methoxyphenyl 34.0 DIDZUO (Dey et al, 2018) 3-chloro-7-methyl-imidazo[1,2-a]pyridinyl phenyl 28.0 ECEGEA (Ma et al, 2011) ethyl 8-methyl-imidazo[1,2-a]pyridinyl-3-carboxylate phenyl 44.2 HUPWIZ01 (Vega et al, 2011) N,N-dimethyl-2-(6-methyl-imidazo[1,2-a]pyridin-3-yl)acetamide 4-methylphenyl 24.6…”

Section: Energy Frameworkmentioning

confidence: 99%

Crystal structure, DFT calculation, Hirshfeld surface analysis and energy framework study of 6-bromo-2-(4-bromophenyl)imidazo[1,2-a]pyridine

Khamees¹,

Chaluvaiah²,

El-Khatatneh³

et al. 2019

Acta Crystallogr E Cryst Commun

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Section: Energy Frameworkmentioning

confidence: 99%

Crystal structure, DFT calculation, Hirshfeld surface analysis and energy framework study of 6-bromo-2-(4-bromophenyl)imidazo[1,2-a]pyridine

Khamees¹,

Chaluvaiah²,

El-Khatatneh³

et al. 2019

Acta Crystallogr E Cryst Commun

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“…Their widespread presence underscores their importance in the development of therapeutic agents and highlights the versatile nature of nitrogen heterocycles in medicinal chemistry. [1] Imidazo [1,2a] pyridine, a nitrogen-containing heterocyclic compound, exhibits biological activity across various domains and is prevalent in numerous natural products. Imidazo [1,2-a] pyridine demonstrates a broad spectrum of pharmacological activities, playing a significant role in benzodiazepine and GABA receptor modulation.…”

Section: Introductionmentioning

confidence: 99%

“…These compounds exhibit a diverse range of pharmacological activities, including antitumor, antibiotic, anti‐inflammatory, antidepressant, anti‐HIV, antimicrobial, antibacterial, antifungal, and antiviral properties. Their widespread presence underscores their importance in the development of therapeutic agents and highlights the versatile nature of nitrogen heterocycles in medicinal chemistry [1] …”

Section: Introductionmentioning

confidence: 99%

Amberlyst® A‐26(OH) Ion Exchange Resin Catalyzed Synthesis of Imidazo[1,2a] pyridines/thiazoles in Water and their Further Functionalization

Ghosh,

Nath Barman,

Choudhury

et al. 2024

ChemistrySelect

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Here, we present the development of a synthesis for imidazo[1,2a] pyridine/thiazole derivatives catalyzed by a heterogeneous basic support, specifically Amberlyst® A‐26(OH) ion exchange resin, in a water medium at 60 °C. In pursuit of a green methodology, we opted for this polyionic exchange resin due to its thermal stability and recyclability. Notably, this protocol eliminates the need for strong bases, organic solvents, and additives. The remarkable aspect of this reaction lies in utilizing water as a green solvent, and the synthesized products are easily purified through a straightforward crystallization method. The NMR (1H and 13C) spectroscopy is employed for the characterization of the synthesized products. Furthermore, we explore the additional functionalization of imidazo[1,2a] pyridine/thiazole derivatives.

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Crystal Correlation Of Heterocyclic Imidazo[1,2-a]pyridine Analogues and Their Anticholinesterase Potential Evaluation

Kwong

Kumar

Mah

et al. 2019

Sci Rep

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Imidazo[1,2-a]pyridine-based compounds are clinically important to the treatments of heart and circulatory failures, while many are under development for pharmaceutical uses. In this study, a series of imidazo[1,2-a]pyridine-based derivatives 2(a–o) were synthesized by reacting a-haloketones with 2-aminopyridines in a basic media at ambient temperature. Single crystal X-ray diffraction studies suggest that with low degree-of-freedom, the introduction of bulky adamantyl or electron-rich biphenyl moiety into the imidazopyridine derivatives will not affect its structural occupancy. Imidazo[1,2-a]pyridine-based derivatives with biphenyl side chain are potential AChE inhibitors. Compound 2h which bears a biphenyl side chain and methyl substituent at the position R4 of the imidazo[1,2-a]pyridine ring showed the strongest AChE inhibition with an IC50 value of 79 µM. However, imidazo[1,2-a]pyridine derivatives with phenyl side chain exhibit better BChE inhibition effect among the series. Compound 2j with 3,4-dichlorophenyl side chain and unsubstituted imidazo[1,2-a]pyridine ring appears to be the strongest BChE inhibitor with an IC50 value of 65 µM and good selectivity. The inhibitory effects of active compounds were further confirmed by computational molecular docking studies. The results unveiled that peripheral anionic sites of AChE and acyl pocket of BChE were the predominated binding sites for the subjected inhibitors.

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Crystal structure of 2-(4-methoxyphenyl)-6-nitroimidazo[1,2-a]pyridine-3-carbaldehyde

Cited by 4 publications

References 16 publications

Crystal structure, DFT calculation, Hirshfeld surface analysis and energy framework study of 6-bromo-2-(4-bromophenyl)imidazo[1,2-a]pyridine

Crystal structure, DFT calculation, Hirshfeld surface analysis and energy framework study of 6-bromo-2-(4-bromophenyl)imidazo[1,2-a]pyridine

Amberlyst® A‐26(OH) Ion Exchange Resin Catalyzed Synthesis of Imidazo[1,2a] pyridines/thiazoles in Water and their Further Functionalization

Crystal Correlation Of Heterocyclic Imidazo[1,2-a]pyridine Analogues and Their Anticholinesterase Potential Evaluation

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