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ISRN Organic Chemistry
Volume 2013 (2013), Article ID 791591, 12 pages
http://dx.doi.org/10.1155/2013/791591
Research Article

Synthesis, Characterization, and BSA Binding Studies of Some New Benzamides Related to Schiff Base

1Department of Chemistry, University of Mysore, Manasagangotri, Mysore, Karnataka 570006, India
2Department of Botany, University of Mysore, Manasagangotri, Mysore, Karnataka 570006, India

Received 12 February 2013; Accepted 7 March 2013

Academic Editors: G. Gattuso, M. Parra, and F. L. Van Delft

Copyright © 2013 M. K. Prashanth et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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.