A Comprehensive Study of the Synthesis, Spectral Characteristics, Quantum–Chemical Molecular Electron Density Theory, and In Silico Future Perspective of Novel CBr3-Functionalyzed Nitro-2-Isoxazolines Obtained via (3 + 2) Cycloaddition of (E)-3,3,3-Tribromo-1-Nitroprop-1-ene DOI Creative Commons

Karolina Zawadzińska-Wrochniak,

Karolina Kula, Mar Ríos‐Gutiérrez

и другие.

Molecules, Год журнала: 2025, Номер 30(10), С. 2149 - 2149

Опубликована: Май 13, 2025

The search for new heterocyclic compounds with biological potential is one of the current challenges in modern chemistry. Therefore, comprehensive study (3 + 2) cycloaddition (32CA) reactions between a series aryl-substituted nitrile N-oxides (NOs) and (E)-3,3,3-tribromo-1-nitroprop-1-ene (TBNP) carried out. According to experimental research, all tested 32CAs, proper (4RS,5RS)-3-aryl-4-nitro-5-tribromomethyl-2-isoxazolines are obtained as only reaction product. In turn, quantum-chemical MEDT shows that creation heterocycles occur via polar attack zwitterionic moderate-nucleophilic NOs strong electrophilic TBNP. realized according two-stage, one-step asynchronous mechanism, which formation O-C(CBr3) bond takes place once C-C(NO2) already formed. What more, computational analysis confirmed results. At end, 2-isoxazolines were docked three proteins: gelatinase B, cyclooxygenase COX-1, Caspase-7. We hope presented will be helpful searching future direction application this class organic compounds.

Язык: Английский

A Comprehensive Study of the Synthesis, Spectral Characteristics, Quantum–Chemical Molecular Electron Density Theory, and In Silico Future Perspective of Novel CBr3-Functionalyzed Nitro-2-Isoxazolines Obtained via (3 + 2) Cycloaddition of (E)-3,3,3-Tribromo-1-Nitroprop-1-ene DOI Creative Commons

Karolina Zawadzińska-Wrochniak,

Karolina Kula, Mar Ríos‐Gutiérrez

и другие.

Molecules, Год журнала: 2025, Номер 30(10), С. 2149 - 2149

Опубликована: Май 13, 2025

The search for new heterocyclic compounds with biological potential is one of the current challenges in modern chemistry. Therefore, comprehensive study (3 + 2) cycloaddition (32CA) reactions between a series aryl-substituted nitrile N-oxides (NOs) and (E)-3,3,3-tribromo-1-nitroprop-1-ene (TBNP) carried out. According to experimental research, all tested 32CAs, proper (4RS,5RS)-3-aryl-4-nitro-5-tribromomethyl-2-isoxazolines are obtained as only reaction product. In turn, quantum-chemical MEDT shows that creation heterocycles occur via polar attack zwitterionic moderate-nucleophilic NOs strong electrophilic TBNP. realized according two-stage, one-step asynchronous mechanism, which formation O-C(CBr3) bond takes place once C-C(NO2) already formed. What more, computational analysis confirmed results. At end, 2-isoxazolines were docked three proteins: gelatinase B, cyclooxygenase COX-1, Caspase-7. We hope presented will be helpful searching future direction application this class organic compounds.

Язык: Английский

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