Synthesis and membrane-protective activity of 2,6-diisobornylphenol derivatives with N- and O-containing fragments at position 4

• Published in: Russian chemical bulletin Vol. 66; no. 2; pp. 297 - 303
• Main Authors: Buravlev, E. V., Chukicheva, I. Yu, Shevchenko, O. G., Kutchin, A. V.
• Format: Journal Article
• Language: English
• Published: New York Springer US 01-02-2017; Springer Nature B.V
• Subjects: Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Derivatives; Erythrocytes; Fragmentation; Fragments; Full Articles; Inorganic Chemistry; Mice; Organic Chemistry; Pharmacology; Synthesis; Toxicity; red blood cells; oxidative hemolysis; amides; 2,6-diisobornyl-4-methylphenol; membrane-protective activity; antioxidant activity
• ISSN: 1066-5285; 1573-9171
• DOI: 10.1007/s11172-017-1731-x

Two series of new amide derivatives containing 2,6-diisobornylphenol moiety were synthesized based on 3,5-diisobornyl-4-hydroxybenzoic acid and 4-butylaminomethyl-2,6-diisobornylphenol. Toxicity, membrane-protective (MP) and antioxidant (AO) activity of the obtained compounds were evaluated using red blood cells of laboratory mice as the test object. The tests demonstrated the absence of hemolytic activity for all the synthesized derivatives and the presence of high MP and AO activity under conditions of acute H
2
O
2
-induced oxidative stress for (3,5-diisobornyl-4-hydroxyphenyl)(morpholino)methanone and
N
-
n
-butyl-
N
-(3,5-diisobornyl-4-hydroxybenzyl)acetamide. A comparison of the data of the newly obtained compounds and those of described earlier 2,6-diisobornylphenol derivatives with
N
- and
O
-containing fragments at position 4 (alkoxymethyl, carboxy, and aminomethyl derivatives) led to a conclusion that the most promising for further studies of pharmacological activity are compounds containing methoxycarbonyl, methoxymethyl, ethoxymethyl, morpholinomethyl, di-
n
-butylaminomethyl, (azepan-1-yl)methyl, or
N
-acetyl-
N
-alkylaminomethyl function, which provide low toxicity and high MP and AO activity.