Synthesis and anti lipid-peroxidation activity of hydroquinone monoalkyl ethers.
A series of hydroquinone monoalkyl ethers was synthesized and evaluated for anti lipid-peroxidation activity in rat liver microsomes. 4-Hexyloxy-2,3,6-trimethylphenol (9), having a low redox potential, as well as ascorbic acid exhibited the strongest anti lipid-peroxidation activity (IC50 = 4.2 x 10(-7) M). Structure-activity relationship studies demonstrated that the inhibitory effect of hydroquinone monoalkyl ethers on lipid peroxidation was increased by the acquisition of an optimum hydrophobicity and decreased by an insufficient or excessive hydrophobicity.
Nihro
Y
Y
Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Japan.
Furukawa
H
H
Sogawa
S
S
Wang
T C
TC
Miyataka
H
H
Matsumoto
H
H
Miki
T
T
Satoh
T
T
D000818:Animals; D006873:Hydroquinones / Q000138:chemical synthesis* / Q000494:pharmacology; D066298:In Vitro Techniques; D015227:Lipid Peroxidation / Q000187:drug effects*; D008862:Microsomes, Liver / Q000187:drug effects / Q000378:metabolism; D010647:Phenyl Ethers / Q000138:chemical synthesis* / Q000494:pharmacology; D051381:Rats; D013329:Structure-Activity Relationship
D006873:Hydroquinones; D010647:Phenyl Ethers