Synthesis, Characterization, DFT Mechanistic Study, Antimicrobial Activity, Molecular Modeling, and ADMET Properties of Novel Pyrazole-isoxazoline Hybrids

ACS Omega, Journal Year: 2022, Volume and Issue: 7(50), P. 46731 - 46744

Published: Dec. 8, 2022

A series of new heterocycle hybrids incorporating pyrazole and isoxazoline rings was successfully synthesized, characterized, evaluated for their antimicrobial responses. The synthesized compounds were obtained utilizing N-alkylation 1,3-dipolar cycloaddition reactions, as well structures established through spectroscopic methods confirmed by mass spectrometry. To get more light on the regioselective synthesis hybrid compounds, mechanistic studies performed using DFT calculations with B3LYP/6-31G(d,p) basis set. Additionally, results preliminary screening indicate that some examined showed potent activity, compared to standard drugs. confirm activity is strongly dependent nature substituents linked rings. Furthermore, molecular docking conducted highlight interaction modes between investigated Escherichia coli Candida albicans receptors. Notably, demonstrate have strong protein binding affinities. stability formed complexes compound 6c, target proteins also a 100 ns dynamics simulation. Finally, prediction ADMET properties suggests almost all possess good pharmacokinetic profiles no signs observed toxicity, except 6e, 6f, 6g.

Language: Английский

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Asymmetric [4 + 3] Annulations for Constructing Divergent Oxepane Frameworks via Cooperative Tertiary Amine/Transition Metal Catalysis

Organic Letters, Journal Year: 2021, Volume and Issue: 23(21), P. 8559 - 8564

Published: Oct. 26, 2021

We report asymmetric [4 + 3] annulations between isatin-derived Morita–Baylis–Hillman carbonates and two types of vinyl synergistically catalyzed by tertiary amines transition metals, through chemoselective assemblies in situ formed allylic ylides metal-containing 1,4-dipoles. A range oxepane frameworks are generally constructed moderate to good yields with high stereocontrol. Moreover, all four diastereomers for the products bearing vicinal stereocenters accessible tuning amine metal catalysts.

Language: Английский

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Synthesis, Characterization, DFT Mechanistic Study, Antibacterial Activity, Molecular Modeling, and ADMET Properties of Novel Chromone-Isoxazole Hybrids

Journal of Molecular Structure, Journal Year: 2024, Volume and Issue: 1314, P. 138770 - 138770

Published: May 30, 2024

Language: Английский

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Organocatalytic Strategies for the Development of the Enantioselective Inverse‐electron‐demand Hetero‐Diels‐Alder Reaction

Chemistry - A European Journal, Journal Year: 2021, Volume and Issue: 27(49), P. 12509 - 12520

Published: June 16, 2021

Cycloaddition reactions, in particular Diels-Alder have attracted a lot of attention from organic chemists since they represent one the most powerful methodologies for construction carbon-carbon bonds. In particular, inverse-electron-demand hetero-Diels-Alder reactions been an important breakthrough synthesis heterocyclic compounds. Among all their variants, organocatalytic enantioselective version has widely explored asymmetric diversely functionalized scaffolds under reaction conditions encompassed within green chemistry field is great interest. this review, profound revision on latest advances inverse-electron demand shown.

Language: Английский

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Recent advances in tertiary amine Lewis base-promoted cycloadditions of allenoates

Chinese Chemical Letters, Journal Year: 2021, Volume and Issue: 33(5), P. 2372 - 2382

Published: Nov. 19, 2021

Language: Английский

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Diastereodivergentcis- andtrans-fused [4 + 2] annulations of cyclic 1,3-dienes and 1-azadienesvialigand-controlled palladium catalysis

Chemical Science, Journal Year: 2023, Volume and Issue: 14(7), P. 1896 - 1901

Published: Jan. 1, 2023

Diastereodivergent and asymmetric [4 + 2] annulations between cyclic 1,3-dienes 1-azadienes via ligand-controlled Pd catalysis have been realized, furnishing both cis - trans -fused tetrahydropyridines in good yields stereoselectivity levels.

Language: Английский

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Perfluoroarene Interaction-Controlled Chiral Phosphoric Acid-Catalyzed Enantioselective Michael Addition of Difluoroenoxysilanes to Azadienes: a Combination of Experimental and Theoretical Studies

ACS Catalysis, Journal Year: 2022, Volume and Issue: 12(15), P. 9655 - 9663

Published: July 25, 2022

A catalytic and highly enantioselective Mukaiyama–Michael addition of difluoroenoxysilanes to azadienes has been developed using perfluorinated aryl-incorporating chiral monophosphoric acid (PF-CPA) as an effective, multipoint-controlled catalyst. The inherent perfluoroaryl substituent is finely beneficial not only for achieving high activity but also creating a compact confined environment transformations. Theoretical studies showed that the π–π interaction hydrogen bond between PF-CPA substrates play crucial role in determining stereochemical outcomes comparison with those phenyl, binaphthyl, partially fluorinated aryls.

Language: Английский

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CuI nanoparticles-immobilized on a hybrid material composed of IRMOF-3 and a sulfonamide-based porous organic polymer as an efficient nanocatalyst for one-pot synthesis of 2,3-disubstituted benzo[b]furans

Arabian Journal of Chemistry, Journal Year: 2023, Volume and Issue: 16(8), P. 104975 - 104975

Published: May 13, 2023

This study was conducted to synthesize and characterize a new polymer/metal–organic framework (MOF) stabilizer via the reaction between sulfonamide-triazine-based porous organic polymer (poly(sulfonamide-triazine)) (PSTA) an amino-functionalized zinc metal–organic (IRMOF-3). Next, prepared nanocomposites (IRMOF-3/PSTA/Cu) were modified using copper iodide nanoparticles (CuI NPs). The composites characterized by FT-IR, XRD, EDX, N2 adsorption–desorption, TGA, SEM, TEM, XPS analysis. Finally, application of investigated through one-pot synthesis 2,3-disubstituted benzo[b]furans. To this end, alkyne, salicylaldehydes, amines subjected three-component domino reaction. All products obtained in high turnover frequency (TOF) up 142.42, suggesting catalyst's selectivity activity mentioned reactions. synthesized nanocatalyst is reusable seven times with no considerable catalytic efficiency loss. Overall, yields products, nanocatalyst's facile recovery, short time, wide substrate scopes make procedure eco-friendly, practical, economically justified.

Language: Английский

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Asymmetric [3 + 2] cycloaddition of donor–acceptor cyclopropanes with azadienes enabled by Brønsted base catalysis

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(10), P. 2905 - 2910

Published: Jan. 1, 2024

A chiral bifunctional Brønsted base-catalyzed enantioselective [3 + 2] cycloaddition of D–A cyclopropanes and azadienes is reported. The protocol features broad substrate scope, mild reaction conditions high functional group tolerance.

Language: Английский

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Transition-metal-free regioselective synthesis of spiro-oxazolidines through [3 + 2] annulation reactions of azadienes with haloalcohols

RSC Advances, Journal Year: 2025, Volume and Issue: 15(14), P. 10634 - 10638

Published: Jan. 1, 2025

The transition-metal-free regioselective [3 + 2] annulation of azadienes with haloalcohols for the preparation highly functionalized spiro-oxazolidines is experimentally simple, broad substrate scope, good yields, and excellent regioselectivity.

Language: Английский

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