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Journal of Chemistry
Volume 2015, Article ID 465286, 9 pages
http://dx.doi.org/10.1155/2015/465286
Research Article

Synthesis, Characterization, and Pharmacological Evaluation of Selected Aromatic Amines

1Department of Biochemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan
2Department of Pharmacy, Quaid-i-Azam University, Islamabad 45320, Pakistan
3Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan

Received 3 December 2014; Revised 24 January 2015; Accepted 25 January 2015

Academic Editor: Shu Taira

Copyright © 2015 Hammad Ismail 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

Aromatic amines 1-amino-4-phenoxybenzene (A-1A), 2-(4-aminophenoxy) naphthalene (A-2A), and 1-(4-aminophenoxy) naphthalene (A-3A) were synthesized by the reduction of corresponding nitroaromatics with hydrazine monohydrate and Pd/C 5% (w/w). The newly synthesized compounds were characterized by FTIR, 1H NMR, 13C NMR, UV-visible spectrophotometer, and mass spectrometry and their biological activities were investigated along with structurally similar 4-(4-aminophenyloxy) biphenyl (A-A). Results of brine shrimp cytotoxicity assay showed that almost all of the compounds had LD50 values <1 μg/mL. The compounds also showed significant antitumor activity with IC50 values ranging from 67.45 to 12.2 µgmL−1. The cytotoxicity and antitumor studies correlate the results which suggests the anticancerous nature of compounds. During the interaction study of these compounds with DNA, all of the compounds showed hyperchromic effect indicating strong interaction through binding with the grooves of DNA. Moreover, A-3A also showed decrease in confirming higher propensity for DNA groove binding. In DPPH free radical scavenging assay, all the compounds showed potential antioxidant capability. The compounds were highly active in protecting DNA against hydroxyl free radicals. DNA interaction and antioxidant results back up each other indicating that these compounds have potential to be used as cancer chemopreventive agents. Additionally, one compound (A-1A) showed significant antibacterial and antifungal activity as well.