A Comprehensive Study of the Synthesis, Spectral Characteristics, Quantum–Chemical Molecular Electron Density Theory, and In Silico Future Perspective of Novel CBr<sub>3</sub>-Functionalyzed Nitro-2-Isoxazolines Obtained via (3 + 2) Cycloaddition of (<i>E</i>)-3,3,3-Tribromo-1-Nitroprop-1-ene

A Comprehensive Study of the Synthesis, Spectral Characteristics, Quantum–Chemical Molecular Electron Density Theory, and In Silico Future Perspective of Novel CBr<sub>3</sub>-Functionalyzed Nitro-2-Isoxazolines Obtained via (3 + 2) Cycloaddition of (<i>E</i>)-3,3,3-Tribromo-1-Nitroprop-1-ene

The search for new heterocyclic compounds with biological potential is one of the current challenges in modern chemistry. Therefore, the comprehensive study of (3 + 2) cycloaddition (32CA) reactions between a series of aryl-substituted nitrile N-oxides (NOs) and (<i>E</i>)-3,3,3-tribromo...

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Main Authors: Karolina Zawadzińska-Wrochniak, Karolina Kula, Mar Ríos-Gutiérrez, Bartłomiej Gostyński, Tomasz Krawczyk, Radomir Jasiński
Format: Article
Language:English
Published: MDPI AG 2025-05-01
Series:Molecules
Subjects:
(3 + 2) cycloaddition
nitrile oxide
nitroalkene
molecular mechanism
molecular electron density theory
molecular docking
Online Access:https://www.mdpi.com/1420-3049/30/10/2149
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Summary:The search for new heterocyclic compounds with biological potential is one of the current challenges in modern chemistry. Therefore, the comprehensive study of (3 + 2) cycloaddition (32CA) reactions between a series of aryl-substituted nitrile N-oxides (NOs) and (<i>E</i>)-3,3,3-tribromo-1-nitroprop-1-ene (TBNP) is carried out. According to the experimental research, in all tested 32CAs, the proper (4<i>RS</i>,5<i>RS</i>)-3-aryl-4-nitro-5-tribromomethyl-2-isoxazolines are obtained as only one reaction product. In turn, the quantum–chemical MEDT study shows that the creation of heterocycles occur via the polar attack of zwitterionic moderate-nucleophilic NOs to strong electrophilic TBNP. The reactions are realized according to a two-stage, one-step asynchronous mechanism, in which the formation of the O-C(CBr<sub>3</sub>) bond takes place once the C-C(NO<sub>2</sub>) bond is already formed. What is more, the computational analysis confirmed the experimental results. At the end, the obtained 2-isoxazolines were docked to three proteins: gelatinase B, cyclooxygenase COX-1, and Caspase-7. We hope that the presented study will be helpful for searching for the future direction of application for this class of organic compounds.
ISSN:1420-3049

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