Novel Aminomethyl Derivatives of 4-Methyl-2-prenylphenol: Synthesis and Antioxidant Properties

被引：10

作者：

Buravlev, Evgeny V. ^{[1
]}

Fedorova, Irina V. ^{[1
]}

Shevchenko, Oksana G. ^{[2
]}

Kutchin, Aleksandr V. ^{[1
]}

机构：

[1] Russian Acad Sci, Ural Branch, Inst Chem, Komi Sci Ctr, 48 Pervomayskaya St, Syktyvkar 167000, Komi Republic, Russia

[2] Russian Acad Sci, Ural Branch, Inst Biol, Komi Sci Ctr, 28 Kommunisticheskaya St, Syktyvkar 167982, Komi Republic, Russia

来源：

CHEMISTRY & BIODIVERSITY | 2019年 / 16卷 / 03期

关键词：

alkylation; Mannich bases; antioxidant activity; red blood cells; oxidative hemolysis; synthesis design; MEMBRANE-PROTECTIVE ACTIVITY; BIOLOGICAL EVALUATION; MANNICH-BASES; IN-VITRO; XANTHONES; DAMAGE;

D O I：

10.1002/cbdv.201800637

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

4-Methyl-2-prenylphenol (1) was synthesized from para-cresol and prenol, natural alcohol under the conditions of heterogeneous catalysis. A series of nine new aminomethyl derivatives with secondary and tertiary amino groups were obtained on the basis of compound 1. A comparative evaluation of their antioxidant properties was carried out using in vitro models. It was established that Mannich base with octylaminomethyl group has radical-scavenging activity, high Fe2+-chelation ability as well as the ability to inhibit oxidative hemolysis of red blood cells.

引用

页数：10

共 32 条

[1] Antioxidant effect of alkynylselenoalcohol compounds on liver and brain of rats in vitro [J].

Acker, Carmine Ines ;

Brandao, Ricardo ;

Rosario, Alisson Rodrigues ;

Nogueira, Cristina Wayne .

ENVIRONMENTAL TOXICOLOGY AND PHARMACOLOGY, 2009, 28 (02) :280-287

[2] New Prenylated ortho-Dihydroxycoumarins from the Fruits of Ficus nipponica [J].

Akihara, Yui ;

Ohta, Emi ;

Nehira, Tatsuo ;

Omura, Hisashi ;

Ohta, Shinji .

CHEMISTRY & BIODIVERSITY, 2017, 14 (09)

[3]

ASAKAWA T, 1980, LIPIDS, V15, P137, DOI 10.1007/BF02540959

[4]

Buege J A, 1978, Methods Enzymol, V52, P302

[5] Synthesis and membrane-protective activity of 4-aminomethyl derivatives of 2,6-diisobornylphenol [J].

Buravlev, E. V. ;

Chukicheva, I. Yu. ;

Shevchenko, O. G. ;

Suponitskii, K. Yu. ;

Kutchin, A. V. .

RUSSIAN CHEMICAL BULLETIN, 2017, 66 (01) :91-98

[6] Novel Mannich bases of α- and γ-mangostins: Synthesis and evaluation of antioxidant and membrane-protective activity [J].

Buravlev, Evgeny V. ;

Shevchenko, Oksana G. ;

Anisimov, Aleksei A. ;

Suponitsky, Kyrill Yu .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2018, 152 :10-20

[7] Synthesis and membrane-protective activity of novel derivatives of α-mangostin at the C-4 position [J].

Buravlev, Evgeny V. ;

Shevchenko, Oksana G. ;

Kutchin, Aleksandr V. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2015, 25 (04) :826-829

[8] SELECTIVE REACTIONS BETWEEN PHENOLS AND FORMALDEHYDE - A NOVEL ROUTE TO SALICYLALDEHYDES [J].

CASIRAGHI, G ;

CASNATI, G ;

PUGLIA, G ;

SARTORI, G ;

TERENGHI, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (09) :1862-1865

[9] Secondary metabolites from the root of Ehretia longiflora and their biological activities [J].

Chien, Yu-Chieh ;

Lin, Chu-Hung ;

Chiang, Michael Y. ;

Chang, Hsun-Shuo ;

Liao, Chang-Hui ;

Chen, Ih-Sheng ;

Peng, Chien-Fang ;

Tsai, Ian-Lih .

PHYTOCHEMISTRY, 2012, 80 :50-57

[10] Influence of non-steroidal anti-inflammatory drugs on Drosophila melanogaster longevity [J].

Danilov, Anton ;

Shaposhnikov, Mikhail ;

Shevchenko, Oksana ;

Zemskaya, Nadezhda ;

Zhavoronkov, Alex ;

Moskalev, Alexey .

ONCOTARGET, 2015, 6 (23) :19428-19444

← 1 2 3 4 →