α-Phenyl-N-cyclohexyl Nitrones: Preparation and Use as Spin-Traps
| Autor: | Pierre-André Klein, Grégory Durand, Kamal Zéamari, Béatrice Tuccio, Fanny Choteau, Marie Rosselin |
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| Přispěvatelé: | Equipe Chimie Bioorganique et Systèmes Amphiphiles, Avignon Université (AU), Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM), Institut de Chimie Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS) |
| Rok vydání: | 2016 |
| Předmět: |
chemistry.chemical_classification
Spin trapping 010405 organic chemistry Chemistry Organic Chemistry 010402 general chemistry Ring (chemistry) Photochemistry 01 natural sciences Medicinal chemistry 0104 chemical sciences Nitrone Benzaldehyde chemistry.chemical_compound Nitro Michael reaction [CHIM]Chemical Sciences Reactivity (chemistry) Bifunctional ComputingMilieux_MISCELLANEOUS |
| Zdroj: | Journal of Organic Chemistry Journal of Organic Chemistry, American Chemical Society, 2016, 82 (1), pp.135-142. ⟨10.1021/acs.joc.6b02262⟩ Journal of Organic Chemistry, 2016, 82 (1), pp.135-142. ⟨10.1021/acs.joc.6b02262⟩ |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/acs.joc.6b02262 |
| Popis: | Two bifunctional α-phenyl-N-cyclohexyl nitrones were synthesized with the expectation that the cyclohexyl ring will impart lipophilicity to the molecule, high reactivity to the nitronyl group, and stability to the spin adducts formed. The synthesis of the acid nitrone 4 and its corresponding tert-butyl ester 3 was initiated by a Michael reaction to introduce the cyclohexyl ring. A Zn/AcOH-mediated reduction of the nitro functionality followed by condensation onto benzaldehyde generated the nitronyl function. In agreement with their high lipophilicity values, nitrone 3 was insoluble in water, while nitrone 4 exhibited a poor water solubility. It was determined that the presence of the cyclohexyl ring did not affect either the reduction or oxidation potentials of the nitronyl group in comparison to the classical α-phenyl-N-tert-butylnitrone (PBN). The spin trapping ability of 3 and 4 was investigated by EPR for oxygen- and carbon-centered radicals. In most cases, the nitrones gave rise to a standard six-line EPR spectrum whose values were in agreement with the literature, accompanied by a minor second species. In DMSO, the half-lives of nitrone 3 and 4-OOH adducts were double that of PBN, suggesting that the stabilization comes from the cyclohexyl ring and/or the electronic effect of the carboxylic acid. |
| Databáze: | OpenAIRE |
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