Copper(II)-photocatalyzed Hydrocarboxylation of Schiff bases with CO 2 : antimicrobial evaluation and in silico studies of Schiff bases and unnatural α-amino acids

• Published in: Journal of biomolecular structure & dynamics 2024-01, p.1-14
• Main Authors: Gordon, Allen T, Hosten, Eric C, van Vuuren, Sandy, Ogunlaja, Adeniyi S
• Format: Article
• Language: English
• ISSN: 0739-1102; 1538-0254
• DOI: 10.1080/07391102.2024.2301765

We synthesized and characterized two copper(II) complexes: and , where  = 2,2'-bipyridine and L' = 4,4'-dimethyl-2,2'-bipyridine. We evaluated their photocatalytic hydrocarboxylation properties on a series of synthesized Schiff bases ( ): (E)-1-(4-((5-bromo-2-hydroxybenzylidene)amino)phenyl)ethanone ( ), (E)-N-(4-(dimethylamino)benzylidene)benzo[d]thiazol-2-amine ( ), (E)-4-Bromo-2-((thiazol-2-ylimino)methyl)phenol ( ), and (E)-4-((5-bromo-2-hydroxybenzylidene)amino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one ( ). Under mild photocatalytic reaction conditions (room temperature, 1 atm CO , 30-watt Blue LED light), the derivatives of α-amino acids were obtained with yields ranging from 5% to 44%. Experimental results demonstrated that exhibited superior photocatalytic efficiency compared to , attributed to favourable electronic properties. In silico studies revealed strong binding strengths with E. faecalis DHFR (4M7U) for docked Schiff bases ( ) and unnatural α-amino acids ( ). studies further demonstrated significant antimicrobial and antifungal activity for , , and , while none of the synthesized exhibited such properties, primarily due to the electronic and binding properties of these molecules.Communicated by Ramaswamy H. Sarma.