Synthesis, biological evaluation of antioxidant-antibacterial activities and computational studies of novel anthracene- and pyrene-based Schiff base derivatives

Abstract

Schiff base derivatives with anthracene- and pyrene-based units, A1-A6 and P1-P6 were synthesized (89%–99% yields). Schiff base derivatives were designed to possess an heterocyclic moiety on one side to enhance the coordination ability towards metals. To investigate the biological assay of the newly synthesized compounds, their DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging, metal chelating, reducing power, antibacterial and DNA binding activities were tested. A6 (63.1%) showed the maximum free radical scavenging activity among all. However, compound P3 at concentration of 200 μg/mL possessed the highest metal chelating (45.8%) activity and power of reduction. In addition, P3 and A6 showed antibacterial activity against all bacteria tested and both compounds were very well bound to CT-DNA. Density functional theory method with B3LYP/6-311++G(d,p) basis set was performed to get information about the structural and electronic properties of the present compounds. In addition, the metal coordination properties of the dimers of the parent Schiff bases were investigated through interactions with Zn 2+ .

A Review on the Antimicrobial Activity of Schiff Bases: Data Collection and Recent Studies

“…Recently, Gümüş et al (2020) [ 49 ] described two series of SB derivatives with anthracene- and pyrene-based units, which were synthesized and evaluated for their antibacterial activity against Gram-negative Bacillus cereus, E. coli and Pseudomonas aeruginosa . These experiments were performed by using the disk diffusion method taking tetracycline (30 μg) and streptomycin (10 μg) discs as positive controls.…”

Pharmacological Activities of Schiff Bases and Their Derivatives with Low and High Molecular Phosphonates

“…Many of the anthracene-based compounds showed better free radical elimination, metal chelating, reducing power, antimicrobial and DNA binding capacity compared to the pyrene-based derivatives. Three of the systems demonstrate higher antioxidant activities than all of the pyrene-containing compounds [ 10 ].…”

“…One of the most important properties of Schiff bases is their selectivity toward metal ions and ability to form complexes, including highly stable 4-, 5- and 6-ring complexes. Just like the Schiff bases, their metal complexes also possess anticancer, antibacterial, antifungal and antiviral properties [ 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 ]. In biology, the Schiff bases play a very important role as a transport agent in amino acid biosynthesis ( Scheme 2 ) [ 2 ].…”

Polycyclic aromatic‐based fluorescent probes: Color properties and fluorimetric detection of nitroaromatic explosives

“…Compounds A-C containing polyaromatics were synthesized in coherence with the literature. [31,32] For this, 0.57 g (5 mmol) of cyclohexane-1,4-diamine was dissolved in methanol. It was kept in a magnetic stirrer for a certain period of time.…”