ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Mannich bases of alizarin: synthesis and evaluation of antioxidant capacity

Evgeny V. Buravlev and Oksana G. Shevchenko

Institute of Chemistry, Komi Scientific Center, Ural Branch of the Russian Academy of Sciences, Syktyvkar, Russian Federation

E-mail: eugeneburavlev@gmail.com

Received: 13 April 2022  Accepted: 13 September 2022

Abstract:

In this work, a series of C-3-aminomethyl derivatives based on alizarin (1) was obtained using Mannich reaction. The antioxidant properties of the compounds were evaluated using in vitro models. It was found that most of the synthesized derivatives were superior to alizarin (1) in radical scavenging activity and Fe²⁺-chelation ability. The antioxidant activity of alizarin derivatives was confirmed using biologically relevant test systems; all compounds strongly inhibited Fe²⁺/ascorbate-initiated oxidation of unsaturated fatty acids of animal lipids and most of them increased the survival of red blood cells under conditions of acute oxidative stress. In the cellular model system, the Mannich base containing a thiomorpholinomethyl moiety demonstrated the highest activity.

Graphical abstract

Keywords: Alizarin; Mannich bases; Antioxidants; Oxidative hemolysis; Synthesis design

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-022-02492-7

Chemical Papers 77 (1) 499–508 (2023)