Interrelation between the chemical structure and antioxidant properties of N-substituted amides of salicylic acid

Interrelation between the chemical structure and antioxidant properties of N-substituted amides of salicylic acid Full article

Journal

Kinetics and Catalysis
ISSN: 0023-1584 , E-ISSN: 1608-3210

Output data

Year: 2012, Volume: 53, Number: 2, Pages: 162-171 Pages count : DOI: 10.1134/S0023158412020115

Authors

Storozhok N. M. ¹ , Medyanik N. P. ¹ , Krysin A. P. ² , Pozdnyakov I. P. ³ , Krekov S. A. ⁴

Affiliations

1	(Данные Web of science) Tyumen State Med Acad, Tyumen 625023, Russia
2	(Данные Web of science) Russian Acad Sci, Vorozhtsov Inst Organ Chem, Siberian Branch, Novosibirsk 630090, Russia
3	(Данные Web of science) Russian Acad Sci, Inst Chem Kinet & Combust, Siberian Branch, Novosibirsk 630090, Russia
4	(Данные Web of science) Tyumen State Univ, Tyumen 625026, Russia

The kinetics of the initiated oxidation of a model lipid (methyl oleate has been investigated in the presence of a group of new "hybrid" structures, namely, N-substituted amides of salicylic acid whose structure contains an amide residue conjugated with, or separated by a bridging fragment (three methylene groups) from, an N-phenolic substituent. The compounds also differ in the degree of screening of the OH groups. The process was initiated by thermal decomposition of azobisisobutyronitrile at 60A degrees C (initiation rate of w (i) = 4.2 x 10(-8) mol L-1 s(-1)) or by UV irradiation (gamma = 313-365 nm, w (i) = 0.6 x 10(-8) mol L-1 s(-1)). The compounds examined exhibit antiradical activity owing to the presence of the phenolic hydroxyl groups. N-substituted salicylamides efficiently inhibit the overall methyl oleate oxidation process and are comparable in activity with dibunolum and alpha-tocopherol or are superior to them. The structures in which the residues of salicylamide and sterically hindered phenol are separated by the bridging fragment are particularly efficient. The advantages of the salicylamides absorbing at 300-365 nm manifest themselves in UV-initiated oxidation. The peroxidase activity of the N-substituted salicyl acid derivatives is determined by the structure of the amide moiety. The compounds examined here are new, promising, effective antioxidants, whose particular structural fragments act via different mechanisms in oxidation.

Storozhok N.M. , Medyanik N.P. , Krysin A.P. , Pozdnyakov I.P. , Krekov S.A.
Interrelation between the chemical structure and antioxidant properties of N-substituted amides of salicylic acid
Kinetics and Catalysis. 2012. V.53. N2. P.162-171. DOI: 10.1134/S0023158412020115 WOS Scopus РИНЦ

Сторожок Н.М. , Медяник Н.П. , Крысин А.П. , Поздняков И.П. , Креков С.А.
Взаимосвязь химической структуры и антиоксидантных свойств n-замещенных амидов салициловой кислоты
Кинетика и катализ. 2012. Т.53. №2. С.170. РИНЦ

Published print:	Apr 1, 2012
Published online:	Apr 2, 2012

Web of science	WOS:000302314300002
Scopus	2-s2.0-84861128703
Elibrary	17985439
OpenAlex	W2033939780