Spirocyclic compounds as innovative tools in drug discovery for medicinal chemists

European Journal of Medicinal Chemistry, Journal Year: 2025, Volume and Issue: 287, P. 117368 - 117368

Published: Feb. 6, 2025

Language: Английский

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Asymmetric synthesis of enantiopure tetracyclic dispirooxindolopyrrolidine-piperidones via microwave-assisted multicomponent reaction: Crystallographic analysis, antimicrobial activity and in silico studies

Journal of Molecular Structure, Journal Year: 2024, Volume and Issue: 1308, P. 138104 - 138104

Published: March 21, 2024

In an attempt towards the development of new antimicrobials, we synthesized by microwave-assisted multicomponent reaction (MCR) enantiopure (E,E)-3,5-bisarylidene-N-[(S)-(-)-methylbenzyl]-4-piperidones, isatin and α-amino esters a series optically active tetracyclic dispirooxindolopyrrolidine-piperidones. The beneficial promising features this protocol such as simple operational procedure, short time (10 min), high product yields (up to 97%) make it efficient eco-friendly approach offering powerful mean expand structural diversity spirooxindoles. This appears hugely advantageous for high-throughput screening processes in drug discovery research. addition, crystallographic parameters inter- intramolecular interactions occurring spiropyrrolidine-fused piperidone derivative 4g were examined through single-crystal XRD analysis allowing determine absolute configuration compound. preliminary biological assessment their antimicrobial activity indicates that most screened products display higher than standard reference drugs Ampicillin Griseofulvin. Some them exhibited good moderate against both bacteria fungi. silico molecular docking predictive ADMET studies spirocompounds carried out. Molecular confirmed binding efficacy candidates 4c 4l low score energy values establishment diverse bonding with site residues. Finally, profiling spiroheterocycles proved remarkable drug-like pharmacokinetic properties.

Language: Английский

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The literature of heterocyclic chemistry, part XXII, 2022

Advances in heterocyclic chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Language: Английский

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Multicomponent synthesis of novel functionalized spiroindenopyridotriazine-4H-pyrans

RSC Advances, Journal Year: 2025, Volume and Issue: 15(9), P. 7103 - 7110

Published: Jan. 1, 2025

A very convenient one-pot method for the synthesis of new biologically active compounds, spiro-4H-pyran derivatives, has been developed. This approach, enables incorporation three pharmacophoric cores: pyran, pyridine and triazine scaffolds, within a single molecular skeleton using an efficient sequential multicomponent reaction. The starting materials include ninhydrin, cyanoacetohydrazide, ethyl cyanoacetate, aromatic aldehydes, pyrazolone malononitrile. In this process, spiropyran derivatives were produced with high efficiency through consecutive reactions. first step involves 1,6-diaminopyridinone via three-component approach readily available materials. second step, pyridotriazine, occurs in domino way without need to separate intermediate product step. Finally, third offers several advantages, including fast simple purification products, use safe solvents, no metallic toxic catalysts, atomic economy excellent chemoselectivity

Language: Английский

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Regioselective cyclocondensations with thiobarbituric acid: spirocyclic and azocine products, X-ray characterization, and antioxidant evaluation

RSC Advances, Journal Year: 2025, Volume and Issue: 15(11), P. 8609 - 8621

Published: Jan. 1, 2025

Multicomponent cyclocondensations of 5-amino-3-methyl-1-phenyl-1H-pyrazole (AMPZ), thiobarbituric acid, and p-formaldehyde under conventional thermal heating or ultrasonic irradiation were studied. Treatment the reaction mixture in ethanol an bath for 3 h produced azocine compound 4b, while same reflux conditions 15 spiro 4a. This work encompasses intricate experimental details, X-ray diffraction measurements, multifaceted computational analyses employing methods such as density functional theory Hirshfeld surface analysis. Crystallographic investigations revealed molecular structure clarified its interactions involving hydrogen bonds weak intermolecular forces. article describes synthesis characterization a novel spirocyclic compound. The study also evaluated antioxidant potential vitro using DPPH ABTS methods. results showed that these compounds best free radical scavenging ability, even very small amounts, at low concentrations, excellent potential. Surprisingly, exhibited strong (ABTS+) activities, mainly attributed to HAT mechanism, indicating their therapeutic agents. Facile multipurpose, three-component selective procedures new spiroheterocycles have been proposed, presenting intriguing perspectives field medicine, particularly antioxidants. geometric values computationally optimized calculated LC-BLYP/6-31(d), aligned with data, reinforcing precision our findings.

Language: Английский

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Introduction to the novel ionic liquid-based catalytic system for the multicomponent preparation of benzo[f]pyrano[3,2-c]chromene and pyrano[3,2-c]chromene derivatives under ultrasonic irradiation condition

Results in Chemistry, Journal Year: 2025, Volume and Issue: unknown, P. 102241 - 102241

Published: April 1, 2025

Language: Английский

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A Diversity‐Oriented Multicomponent Approach to Novel Fused Nitrogen Heterocycles Using 6‐Aminoindazole

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(14)

Published: April 1, 2025

Abstract We present a novel, efficient, eco‐friendly sonochemical strategy for the synthesis of fused nitrogen heterocycles via Brønsted acid‐promoted, one‐pot multicomponent reactions (MCRs). This method involves rapid assembly 6‐aminoindazole, aryl aldehydes, and 1,3‐cyclodione derivatives (barbituric acid, dimedone, 1,3‐dimethyl barbituric acid) under mild identical reaction conditions. The approach delivers diverse range highly functionalized heterocyclic frameworks, including 11‐phenyl‐1,6,7,11‐tetrahydro‐8 H ‐pyrazolo[3,4‐ f ]pyrimido[4,5‐ b ]quinoline‐8,10(9 )‐dione, 8,8‐dimethyl‐11‐phenyl‐1,6,7,8,9,11‐hexahydro‐10 ]acridin‐10‐one, 7,9‐diphenyl‐1,6,7,9‐tetrahydro‐2′ ‐spiro[pyrazolo[3,4‐ ]quinoline‐8,5′‐pyrimidine]‐2′,4′,6′(1′ ,3′ )‐trione derivatives. molecular structures these compounds were unambiguously confirmed through 1H‐NMR, 13C‐NMR single‐crystal X‐ray diffraction (SC‐XRD) analysis. Additionally, control experiments provided valuable mechanistic insights into pathway. protocol stands out its efficiency, high yields, broad functional group tolerance, making it versatile tool diversity‐oriented in modern chemistry.

Language: Английский

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Synthesis of Spirocyclic Phthalans via Ru-Catalyzed [2 + 2 + 2] Cycloaddition of 1,6-Diynes with Ex-Situ Generated Acetylene

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 15, 2025

Spirocyclic motifs are attracting increasing attention owing to their three-dimensional geometries that endow bioactive molecules with superior physical and biological properties. We developed an efficient method for constructing spirocyclic phthalans via the Ru-catalyzed [2 + 2 2] cycloaddition of cycloalkanone-derived 1,6-diynes acetylene gas ex-situ-generated from calcium carbide H2O.

Language: Английский

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L-proline-Brønsted acid deep eutectic mixture (DEM) triggered consecutive Claisen–Schmidt and Michael addition reactions

Research on Chemical Intermediates, Journal Year: 2024, Volume and Issue: 50(3), P. 1273 - 1286

Published: Jan. 27, 2024

Language: Английский

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Synthesis of gem-Difluorinated Oxa/Azaspiro[2.4]heptanes via Palladium-Catalyzed Spirocyclopropanation

Organic Letters, Journal Year: 2024, Volume and Issue: 26(27), P. 5782 - 5787

Published: June 28, 2024

A palladium-catalyzed spirocyclopropanation of

Language: Английский

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