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Takahashi, N. et al.

Takahashi, Tamagawa, Kubo, Fukui, Wakabayashi, Honda,

Enhancement of antioxidant activity of p-alkylaminophenols by alkyl chain elongation.

The initial finding that the p-methylaminophenol (6) exhibited antioxidant activity led us to investigate whether the length of alkyl chains linked to the aminophenol residue might affect antioxidative activity. Therefore, we synthesized p-butylaminophenol (5), p-hexylaminophenol (4), p-octylaminophenol (3), and p-methoxybenzylaminophenol (7). All p-alkylaminophenols quenched alpha,alpha-diphenyl-beta-picrylhydrazyl (DPPH) radicals, with 7 being the most potent DPPH radical scavenger. Lipid peroxidation by rat liver microsomes was reduced by p-alkylaminophenols in dose- and aminophenol alkyl chain length-dependent fashion (3>4>5>6), with 3 being the most potent lipid peroxidation inhibitor, at approximately 350-fold higher potency than 6. These results indicate that elongation of alkyl chains in p-alkylaminophenols may increase antioxidative activity, and that p-alkylaminophenols may potentially be useful in the development of antioxidants.[1]

References

Enhancement of antioxidant activity of p-alkylaminophenols by alkyl chain elongation. Takahashi, N., Tamagawa, K., Kubo, Y., Fukui, T., Wakabayashi, H., Honda, T. Bioorg. Med. Chem. (2003) [Pubmed]

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