An efficient synthesis of new imidazo[1,2-a]pyridine-6-carbohydrazide and pyrido[1,2-a]pyrimidine-7-carbohydrazide derivatives via a five-component cascade reaction

Hosseini, Hajar; Bayat, Mohammad

doi:10.1039/c9ra00350a

Cited by 14 publications

(4 citation statements)

References 38 publications

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“…This result, according to the authors, is due to the fact that when using polar solvents, the reaction is subject to kinetic control, while non-polar solvents contribute to the formation of structure 108, which is more thermodynamically favourable. L. Salhi et al [108] found that 2,3-diaminopyrimidine in the reaction with maleimides acts as a 1,3-N,N-dinucleophile, forming imidazo[1,2-a]pyridines with a wide range of biological activity [111][112][113][114]. As in [23], the authors suggested that the formation of 115 occurs first as a result of nucleophilic attack of the cyclic nitrogen atom of 2,3-diaminopyridine 110 of the double bond of maleimide 1.…”

Section: Reactions With Polynucleophilic Reagents and Involvement In ...mentioning

confidence: 99%

Recyclization of Maleimides by Binucleophiles as a General Approach for Building Hydrogenated Heterocyclic Systems

Vandyshev

Shikhaliev

2022

Molecules

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The building of heterocyclic systems containing hydrogenated fragments is an important step towards the creation of biologically-active compounds with a wide spectrum of pharmacological activity. Among the numerous methods for creating such systems, a special place is occupied by processes using N-substituted maleimides as the initial substrate. This molecule easily reacts in Diels-Alder/retro-Diels-Alder reactions, Michael additions with various nucleophiles, and co-polymerization processes, as have been described in numerous detailed reviews. However, information on the use of maleimides in cascade heterocyclization reactions is currently limited. This study is devoted to a review and analysis of existing literature data on the processes of recyclization of N-substituted maleimides with various C,N-/N,N-/S,N-di- and polynucleophilic agents, such as amidines, guanidines, diamines, aliphatic ketazines, aminouracils, amino- and mercaptoazoles, aminothiourea, and thiocarbomoyl pyrazolines, among others. The significant structural diversity of the recyclization products described in this study illustrates the powerful potential of maleimides as a building block in the organic synthesis of biologically-active compounds with hydrogenated heterocyclic fragments.

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Section: Reactions With Polynucleophilic Reagents and Involvement In ...mentioning

confidence: 99%

Recyclization of Maleimides by Binucleophiles as a General Approach for Building Hydrogenated Heterocyclic Systems

Vandyshev

Shikhaliev

2022

Molecules

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“…Some commercial medications, such as zolpidem, necopidem, minodronic acid, and zolimidine, contain the core component imidazo[1,2-a]pyridine. [16] In recent years, a number of imidazo[1,2-a]pyridine-containing compounds have been described as prospective anticancer treatments, with imidazo[1,2-a]pyridines substituted at the C2 and C3 positions in particular demonstrating significant anticancer activity. [17,18] Imidazo [1,2-a]pyridines have anticancer efficacy by inhibiting CDK, VEGFR, PI3 K, EGFR, topoisomerase II, microtubulin protein, and other enzymes.…”

Section: Introductionmentioning

confidence: 99%

“…Imidazo[1,2‐a]pyridines are also good indole and azaindole bioisosteres. Some commercial medications, such as zolpidem, necopidem, minodronic acid, and zolimidine, contain the core component imidazo[1,2‐a]pyridine [16] . In recent years, a number of imidazo[1,2‐a]pyridine‐containing compounds have been described as prospective anticancer treatments, with imidazo[1,2‐a]pyridines substituted at the C2 and C3 positions in particular demonstrating significant anticancer activity [17,18] .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Imidazo[1,2‐a]pyridine‐Isoquinoline Derivatives as Potent EGFR Inhibiting Anticancer Agents

Gunuguntla,

Hanumantharayappa,

Kumar Koppula

2024

ChemistrySelect

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Herein, we synthesized some new imidazo[1,2‐a]pyridine‐isoquinoline hybrids (8 a–8 x) and investigated their anticancer activity on two human breast cancer cell lines, namely MCF‐7 and MDA‐MB231. Generally, most of them displayed higher activity on both breast cell lines than the reference drug. Specifically, compounds (2,6‐difluorophenyl)(6‐methoxy‐1‐(2‐phenylimidazo[1,2‐a]pyridin‐3‐yl)‐3,4‐dihydroisoquinolin‐2(1H)‐yl)methanone, (6‐methoxy‐1‐(2‐phenyl imidazo[1,2‐a]pyridin‐3‐yl)‐3,4‐dihydroisoquinolin‐2(1H)‐yl)(6‐methoxy pyridin‐3‐yl)methanone, (6‐methoxy‐1‐(2‐phenylimidazo[1,2‐a]pyridin‐3‐yl)‐3,4‐dihydroisoquinolin‐2(1H)‐yl)(pyrimidin‐5‐yl) methanone, 6‐methoxy‐1‐(2‐phenylimidazo[1,2‐a]pyridin‐3‐yl)‐2‐(phenylsulfonyl)‐1,2,3,4‐tetrahydro isoquinoline, 6‐methoxy‐1‐(2‐phenyl imidazo[1,2‐a]pyridin‐3‐yl)‐2‐tosyl‐1,2,3,4‐tetrahydroisoquinoline, and 6‐methoxy‐2‐((4‐methoxyphenyl)sulfonyl)‐1‐(2‐phenylimidazo[1,2‐a] pyridin‐3‐yl)‐1,2,3,4‐tetrahydroisoquinoline showed higher activity against tested cancer cell lines as compared to the erlotinib. The ability of potent compounds to inhibit the tyrosine kinase EGFR was then studied and found that compounds (6‐methoxy‐1‐(2‐phenylimidazo[1,2‐a]pyridin‐3‐yl)‐3,4‐dihydroisoquinolin‐2(1H)‐yl)(pyrimidin‐5‐yl) methanone, 6‐methoxy‐1‐(2‐phenylimidazo[1,2‐a]pyridin‐3‐yl)‐2‐tosyl‐1,2,3,4‐tetra hydroisoquinoline, and 6‐methoxy‐2‐((4‐methoxyphenyl) sulfonyl)‐1‐(2‐phenylimidazo[1,2‐a]pyridin‐3‐yl)‐1,2,3,4‐tetrahydro isoquinoline exhibited promising potency in comparison to the erlotinib. In silico investigations of the most effective compounds were also performed to find interactions with the EGFR receptor that robustly bind to the protein, and energy estimates were in good agreement with the corresponding IC50 values.

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“…The ubiquitous presence of heterocyclic systems containing one, two, three and four nitrogen atoms in five-membered ring viz; pyrrole [4][5][6][7][8], pyrazole [9][10][11][12], imidazole [13][14][15][16][17][18], etc. and the privileged systems containing two nitrogen atoms in a six-membered rings viz.…”

Section: Introductionmentioning

confidence: 99%

One-pot mediated synthesis of pyrimidine and quinazoline annulated derivatives of nitrogen containing five membered rings through their nitrile derivatives as antibacterial agents

A. Gosalia,

Srivastava,

Yaduvanshi

et al. 2023

Bull. Chem. Soc. Eth.

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ABSTRACT. Novel five-membered ring (pyrrole, pyrazole and imidazole)-based pyrimidine and quinazoline derivatives were synthesized by one-pot domino approach. This approach has the advantages of high yield, mild reaction conditions and a simple work-up procedure. The structure of the synthesized compound was elucidated by spectroscopy technique and elemental analysis. The synthesized compound were examined for antimicrobial activity against four bacteria (E. coli, S. pyogenes, S. aureus, and P. aeruginosa) and two fungi (C. albicans and A. clavatus) and most of the synthesized compound exhibited moderate to good activity against reference drug ampicillin, ciprofloxacin, norfloxacin, gentamycin, nystatin and griseofulvin, respectively. KEY WORDS: One-pot, Pyrrole, Pyrazole, Imidazole, Pyrimidine, Quinazoline, Antimicrobial activity Bull. Chem. Soc. Ethiop. 2023, 37(5), 1193-1208. DOI: https://dx.doi.org/10.4314/bcse.v37i5.12

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An efficient synthesis of new imidazo[1,2-a]pyridine-6-carbohydrazide and pyrido[1,2-a]pyrimidine-7-carbohydrazide derivatives via a five-component cascade reaction

Abstract: An easy synthesis of novel and highly substituted imidazo[1,2-a]pyridines and pyrido[1,2-a]pyrimidines using heterocyclic ketene aminals.

Cited by 14 publications

References 38 publications

Recyclization of Maleimides by Binucleophiles as a General Approach for Building Hydrogenated Heterocyclic Systems

Recyclization of Maleimides by Binucleophiles as a General Approach for Building Hydrogenated Heterocyclic Systems

Synthesis of Imidazo[1,2‐a]pyridine‐Isoquinoline Derivatives as Potent EGFR Inhibiting Anticancer Agents

One-pot mediated synthesis of pyrimidine and quinazoline annulated derivatives of nitrogen containing five membered rings through their nitrile derivatives as antibacterial agents

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