STUDY OF ANTIOXIDANT ACTIVITY OF β-AMINOPROPIOAMIDOXIME O-SULFOARIL DERIVATIVES

Abstract

Amidoxime derivatives have a broad spectrum of biological activity. Herein we report the screening of the products of the interaction of β-aminopropioamidoximes [amino group: piperidin-1-yl; morpholin-1-yl; thiomorpholin-1-yl] with para-substituted arylsulfonyl chlorides on antioxidant activity. Antioxidants of non-enzymatic nature are intended to reduce oxidative stress. The most commonly used antioxidants are vitamin C, vitamin E, quercetin, β-carotene. As a rule, antioxidants «quench» free radicals, easily giving protons to active forms of oxygen: singlet oxygen (O•), superoxide anion radical (O2–•), hydrogen peroxide (H2O2•), hydroxyl radical (OH•), peroxyl radical (R-COO•), nitrogen oxide (NO•), peroxynitrite (ONOO•). We determined the antioxidant activity of O-sulfoaryl derivatives of β-aminopropioamidoximes by the DPPH method using quercetin as a reference. Quercetin is able to stabilize an electron radical by several continued conjugation schemes, including C=C and C= O bonds. The percentage of inhibition of the DPPH radical by quercetin is 92.3%. Derivatives of β-(morpholin-1-yl)propioamidoxime with methoxy, methyl, and bromo in the paraposition of the phenyl ring of the sulfogroup lead to 19.31, 11.50, and 10.88% inhibition, respectively; compounds of these series with an unsubstituted phenyl ring and paranitrosubstituent showed inhibition of 7.68% and 5.73% respectively. O-Tosylate β-(thiomorpholin-1-yl)propioamidoxime and O-para-chlorophenylsulfo-β-(morpholin-1-yl)propioamidoxime showed minimal inhibition of 2.38% and 3.70% respectively. O-Tosylate β-(piperidin-1-yl)propioamidoxime did not revealed inhibition.

References

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