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

Abstract:

: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.

journal_name

Int J Mol Sci

authors

Patrascu B,Mocanu S,Coman A,Madalan AM,Popescu C,Paun A,Matache M,Ionita P

doi

10.3390/ijms21103559

subject

Has Abstract

pub_date

2020-05-18 00:00:00

issue

10

issn

1422-0067

pii

ijms21103559

journal_volume

21

pub_type

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