Abstract
Condensation of amine 1 with aldehyde 2 gives Schiff base, N-(4-((benzofuran-2-ylmethylene) amino)phenyl)acetamide 3. Schiff base on N-acylation with different substituted acid chlorides in the presence of triethylamine gives the corresponding benzamides, N-acetyl-N-(4-((benzofuran-2-ylmethylene)amino)phenyl)substitutedbenzamide (NABP) 5a–j. The structures of newly synthesized compounds were characterized by elemental analysis, 1H NMR, 13C NMR FT-IR, and mass spectral studies. Compounds 3 and 5a–j have been screened for their antimicrobial activity using the disc diffusion and minimum inhibitory concentration (MIC) method against the selected bacterial and fungal strain. Compounds 5a, 5e, 5g, and 5h were found to be more active against all tested strains. The antioxidant properties were evaluated by 2,2-diphenyl-1-picrylhydrazyl (DPPH) and superoxide radical scavenging methods. Compounds 5i and 5j showed predominant antioxidant activities among the synthesized analogues. The interaction between NABP and bovine serum albumin (BSA) was investigated using fluorescence and ultraviolet spectroscopic techniques at 298 K under imitated physiological conditions. The results revealed that NABP caused the fluorescence quenching of BSA through a static quenching procedure. The binding constants and the number of binding sites were calculated. The binding distance between the donor (BSA) and acceptor (NABP) was determined based on Forster's theory.
Highlights
Schiff bases represent an important class of organic compounds, especially in the medicinal and pharmaceutical field
The synthesis and characterization of new Schiff bases related to benzamides with antibacterial and antioxidant agents are of great importance for their potential pharmacological use
Synthesis of the desired compound 3 was achieved by condensation of p-aminoacetanilide 1 with 2-benzofurancaroxaldehyde 2 according to the known method [22]
Summary
Schiff bases represent an important class of organic compounds, especially in the medicinal and pharmaceutical field. Schiff bases appear to be important intermediates in a number of enzymatic reactions involving interaction of the amino group of an enzyme, usually that of a lysine residue, with a carbonyl group of the substrate [1]. Schiff bases, derived mostly from variety of heterocyclic rings, were reported to possess a broad spectrum and a wide variety of biological activities including antimicrobial, anti-inflammatory, anticonvulsant, antitumor, and anti-HIV activities [2,3,4]. The Schiff bases have emerged as antimicrobial agents of an immense interest because of their broad spectrum of in-vitro activity and their in vivo chemotherapeutic activity. The synthesis and characterization of new Schiff bases related to benzamides with antibacterial and antioxidant agents are of great importance for their potential pharmacological use
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