Synthesis of Fluorescent Dansyl Derivatives of Methoxyamine and Diphenylhydrazine as Free Radical Precursors.

Bianca Patrascu, Sorin Mocanu, Anca Coman, Augustin M Madalan, Codruta Popescu, Anca Paun, Mihaela Matache, Petre Ionita

International journal of molecular sciences 2020 May 18

filter terms:

Starting from dansyl-chloride, in reaction with 1,1-diphenylhydrazine and methoxyamine, two new fluorescent derivatives 1 and 2 were obtained and characterized by NMR, IR, UV-Vis, HR-MS, and fluorescence spectroscopy. The single-crystal X-ray structure was obtained for compound 2. Both compounds generate free radicals by oxidation, as demonstrated by ESR spectroscopy. Compound 1 generates the corresponding hydrazyl-persistent free radical, evidenced directly by ESR spectroscopy, while compound 2 generates in the first instance the methoxyaminyl short-lived free radical, which decomposes rapidly with the formation of the methoxy radical, evidenced by the ESR spin-trapping technique. By oxidation of compounds 1 and 2, their fluorescence is quenched.

Citation

Bianca Patrascu, Sorin Mocanu, Anca Coman, Augustin M Madalan, Codruta Popescu, Anca Paun, Mihaela Matache, Petre Ionita. Synthesis of Fluorescent Dansyl Derivatives of Methoxyamine and Diphenylhydrazine as Free Radical Precursors. International journal of molecular sciences. 2020 May 18;21(10)