Isobornylchalcones and flavones derived from them: synthesis and antioxidant activity

• Published in: Russian chemical bulletin Vol. 73; no. 6; pp. 1775 - 1788
• Main Authors: Popova, S. A., Krylova, M. V., Pavlova, E. V., Shevchenko, O. G., Chukicheva, I. Yu
• Format: Journal Article
• Language: English
• Published: New York Springer US 01.06.2024; Springer Nature B.V
• Subjects: Antioxidants; Benzene; Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Full Articles; Hydrogen peroxide; Inorganic Chemistry; Organic Chemistry; Synthesis; chalcones; oxidative hemolysis; flavones; antioxidant activity; 2,2-diphenyl-1-picrylhydrazyl (DPPH)
• ISSN: 1066-5285; 1573-9171
• DOI: 10.1007/s11172-024-4295-6

Methoxychalcones containing the NMe 2 , 3,4-(OMe) 2 , 3,4,5-(OMe) 3 , and isobornyl substituents in the B ring were synthesized from 1,3-dihydroxy-4-(1,7,7-trimethylbicyclo-[2.2.1]hept- exo -2-yl)benzene and 1,4-dihydroxy-3-(1,7,7-trimethylbicyclo[2.2.1]hept- exo -2-yl)benzene. Oxidative cyclization of the new isobornylchalcones afforded flavones bearing the 1,7,7-trimethylbicyclo[2.2.1]hept- exo -2-yl moiety. The erythrotoxicity, membrane-protective, and antioxidant activity of the synthesized compounds were evaluated in in vitro models including the model of oxidative hemolysis of mammalian erythrocytes initiated by H 2 O 2 or 2,2′-azobis-(2-amidinopropane) dihydrochloride. All the chalcones studied and most flavones possessed good hemocompatibility and high antioxidant activity. The promise of further research into the synthesis of effective pharmacological substances based on the title compounds was demonstrated.