Multicomponent Assembly of Trisubstituted Imidazoles and Their Photochemical Cyclization into Fused Polyheterocyclic Scaffolds

Gapanenok, Diana; Makhmet, Azat; Peshkov, Anatoly A.; Smirnova, Darya; Amire, Niyaz; Peshkov, Vsevolod A.; Spiridonova, Dar’ya V.; Dar’in, Dmitry; Balalaie, Saeed; Krasavin, Mikhail

doi:10.1021/acs.joc.2c00475

Cited by 9 publications

(4 citation statements)

References 81 publications

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“…to produce imidazole‐based compounds [38] . In the modification of Biginelli, Peshkov and co‐workers recently reported a method to obtain trisubstituted imidazole and zwitterion‐based compounds [39] . In order to determine imidazole‐based compounds with hydrazone moiety and expand the scope of this chemistry to the use of a wide range of previously uncovered imidazole‐based compounds as an outcome of the Biginelli reaction, we present the synthesis of ( HRK1 ‐ 13 ) series in good yields 43–83 %.…”

Section: Resultsmentioning

confidence: 99%

The Suppressive Effect of Novel Hydrazones‐Tethered Imidazoles in HCT‐116 and HT‐29 Colorectal Cancer Cells: Synthesis, Biological Activity and Molecular Modeling Studies

Kekeçmuhammed,

Tapera,

Şahin

et al. 2024

ChemistrySelect

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A series of hybrid compounds containing both the imidazole ring and the hydrazone moiety have been synthesized. Synthesized compounds were characterized by various spectral techniques, including FT‐IR, 1H‐NMR, 13C‐NMR, and HRMS. The compounds were evaluated for their antiproliferative activities on colorectal cancer cells HCT‐116 and HT‐29 in a time‐dependent manner. Among them, some compounds exhibited remarkable anti‐cancer activity with a less cytotoxic effect on non‐cancerous cell lines, especially HRK‐2 with IC50 value of 1.35±0.18 μM in HCT‐116 cells and HRK‐5 with IC50 value of 2.67±0.61 μM in HT‐29 cells. Investigations of colon cancer cell death were performed, and the most active compounds were found to trigger cell death via nuclear localization and induce S phase arrest of the colon cancer cell. Moreover, molecular modeling studies for the synthesized compounds was performed to predict their binding affinities toward the active site of BCL‐2. The findings of the molecular modeling investigations were highly consistent with those of the cytotoxicity results.

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Section: Resultsmentioning

confidence: 99%

The Suppressive Effect of Novel Hydrazones‐Tethered Imidazoles in HCT‐116 and HT‐29 Colorectal Cancer Cells: Synthesis, Biological Activity and Molecular Modeling Studies

Kekeçmuhammed,

Tapera,

Şahin

et al. 2024

ChemistrySelect

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“…Krasavin et al [49] . have demonstrated the cyclization of 2‐oxoaldehydes 1 , 1,3‐dicarbonyl 36 , and acyclic nitrogen bis‐nucleophiles 35 to access the tri‐substituted imidazoles 37 or 38 (Scheme 20) and further 37 or 38 were cyclized photochemically to produce the imidazole‐fused polycyclic compounds.…”

Section: Synthesis Of Imidazolesmentioning

confidence: 99%

“…Krasavin et al [49] have demonstrated the cyclization of 2oxoaldehydes 1, 1,3-dicarbonyl 36, and acyclic nitrogen bisnucleophiles 35 to access the tri-substituted imidazoles 37 or 38 (Scheme 20) and further 37 or 38 were cyclized photochemically to produce the imidazole-fused polycyclic compounds. Upon investigation of the best condition of reaction, a broad range of substrate scope was developed by the utilization of various 2-oxoaldehydes 1, 1,3-dicarbonyl 36, and acyclic nitro-gen bis-nucleophiles 35, and finally, the obtained products were tested for photochemical annulation to obtain the fusedimidazole products.…”

Section: Synthesis Of Imidazoles Through the Multicomponent Reactions...mentioning

confidence: 99%

Recent Advancements in Strategies for the Synthesis of Imidazoles, Thiazoles, Oxazoles, and Benzimidazoles

Kant,

Patel,

Banerjee

et al. 2023

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Nitrogen‐containing heterocycles such as imidazoles, thiazoles, and oxazoles play a significant role in the fields of biological and pharmaceutical chemistry. These compounds were widely used for agrochemical, pesticide, medicinal, and industrial applications. Due to the wide spectrum of structural diversity as well as the biological and pharmaceutical activity of N‐heterocycles, a plethora of reports on their synthesis have appeared in the last few decades. However, developments in various bond‐forming strategies such as C−C, C−N, C−O, C−S, and N−N, as well as C−H activation, have been used as a powerful synthetic tool to derive copious N‐heterocycles. The most prominent and fascinating reports on the synthesis of imidazole, thiazole, oxazoles, and benzimidazole moieties by C−C and C−N coupling reactions, multi‐component and cycloaddition reactions, C−H activation, etc. are discussed in this study. These studies demonstrated the enormous potential of such methods for accelerating modern chemical synthesis and establishing molecular beauty through bonding. The various aspects of the methodologies, like optimized conditions, substrate scope, and mechanistic investigations, are discussed in detail.

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“…Recently, our group has developed a three-component synthesis of trisubstituted imidazoles 9 from nitrogen 1,3-bis-nucleophiles 7 , aryl glyoxals 8 , and cyclic 1,3-dicarbonyl compounds 5 (Scheme c) . The process starts with the condensation of 8 and 5 into Knoevenagel adduct C followed by an aza-Michael addition of 7 and an intramolecular aza-condensation involving glyoxal-originated carbonyl group.…”

Section: Introductionmentioning

confidence: 99%

Substrate-Controlled Three-Component Synthesis of Diverse Fused Heterocycles

et al. 2023

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A chemoselective strategy toward a variety of fused heterocyclic scaffolds relying on a three-component condensation of heterocyclic ketene aminals (HKAs) or corresponding thioaminals with aryl glyoxals and cyclic 1,3-dicarbonyl compounds has been developed and explored. Depending on the applied combination of substrates, the strategy can be tuned to provide straightforward access to imidazo[1,2-a]quinoline, pyrrolo[1,2-a]imidazole, and pyrrolo[2,1-b]thiazole frameworks.

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Multicomponent Assembly of Trisubstituted Imidazoles and Their Photochemical Cyclization into Fused Polyheterocyclic Scaffolds

Cited by 9 publications

References 81 publications

The Suppressive Effect of Novel Hydrazones‐Tethered Imidazoles in HCT‐116 and HT‐29 Colorectal Cancer Cells: Synthesis, Biological Activity and Molecular Modeling Studies

The Suppressive Effect of Novel Hydrazones‐Tethered Imidazoles in HCT‐116 and HT‐29 Colorectal Cancer Cells: Synthesis, Biological Activity and Molecular Modeling Studies

Recent Advancements in Strategies for the Synthesis of Imidazoles, Thiazoles, Oxazoles, and Benzimidazoles

Substrate-Controlled Three-Component Synthesis of Diverse Fused Heterocycles

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