Sodium S [3 (hydroxyaryl)propyl] thiosulfates and [3 (hydroxyaryl)propane] 1 sulfonates with various spatial hindrance of their phenolic ОН groups were synthesized from dialkylphenols via a number of intermediate products. On a model reaction of oxidation of methyl oleate in aqueous sodium dodecyl sulfate, the rate constants of the interaction of the synthesized com pounds with lipoperoxide radicals were determined.A creation of hydrophilic "hybrid" compounds with several antioxidant active centers in the molecule, which can inhibit a peroxidation of lipids in different ways, is one of the priorities in a search of new antioxidants to be used in biology and medicine. Derivatives of spatially hindered phenols, in which para substituent contains alkylammonium, 1-4 isothiuronium, 3,4 and thiosulfate 4,5 groups, are among such compounds. In particular, it was earlier shown that sodium S [3 (3,5 di tert butyl 4 hydroxyphenyl)propyl] thiosulfate (1а) is characterized by a high antioxidant activity due to a concerted action of the phenol and thiosulfate groups 5 and shows hepato protecting, 4 cardioprotecting, 6 and immunomodulating 7 activities.The present work is aimed on the synthesis of struc tural analogs of compound 1а, viz., thiosulfates 1 and sulfonates 2, and on the comparative study of their anti radical activity.Compounds 1 and 2 were obtained from 2,6 dialkyl phenols via the intermediate transformation of the latter to (3 hydroxypropyl)phenols and halogen derivatives 3a-i and 4a-i, respectively.According to the known method, 8 alkylation of 2,6 di tert butylphenol with allyl alcohol in the presence of NaOH gave alcohol 3а, which upon treatment with PBr 3 was converted to bromide 4а, 9 upon treatment with HBr, to bromide 4d, and by thermolysis, to alcohol 3g. 10 Treat ment of the latter with PBr 3 led to bromide 4g (Scheme 1).In contrast to 2,6 di tert butylphenol, its less hindered analogs react with allyl alcohol not that straightforward: a remarkable amount of by products is formed, resulting * Dedicated to the memory of Academician N. N. Vorozhtsov on the 100th anniversary of his birth. R 1 = R 2 = Bu t (а); R 1 = R 2 = cyclo C 6 H 11 (b); R 1 = R 2 = Me (c); R 1 = R 2 = H (d); R 1 = Me, R 2 = Bu t (e); R 1 = Me, R 2 = cyclo C 6 H 11 (f); R 1 = H, R 2 = Bu t (g); R 1 = Н, R 2 = cyclo C 6 H 11 (h)
Sulfonic acids and esters Q 0550 Synthesis and Antioxidant Properties of Sodium S-[3-(Hydroxyaryl)propyl] Thiosulfates and [3-(Hydroxyaryl)propane]-1-sulfonates. -In particular, thiosulfates (IIb,c,d,f) show interesting antiradical activity as hydrophilic antioxidants in the model oxidation of methyl oleate in aqueous sodium dodecyl sulfate solution. -(OLEYNIK, A. S.; KUPRINA, T. S.; PEVNEVA, N. Y.; MARKOV, A. F.; KANDALINTSEVA, N. V.; PROSENKO, A. E.; GRIGOR'EV, I. A.; Russ. Chem.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.
hi@scite.ai
10624 S. Eastern Ave., Ste. A-614
Henderson, NV 89052, USA
Copyright © 2024 scite LLC. All rights reserved.
Made with 💙 for researchers
Part of the Research Solutions Family.