Diaminomaleonitrile-based azo receptors: Synthesis, DFT studies and their antibacterial activities

Khanmohammadi, Hamid and Arab, Vajihe and Rezaeian, Khatereh and Talei, Gholam Reza and Pass, Maryam and Shabani, Nafiseh (2017) Diaminomaleonitrile-based azo receptors: Synthesis, DFT studies and their antibacterial activities. Journal of Molecular Structure, 1129. pp. 169-178.

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Abstract

New unsymmetric diaminomaleonitrile-based azo receptors (H3Ln, n=1-3) have been synthesized via condensation reaction of 5-(4-X-phenyl)-azo-salicyladehyde (X=NO2, OMe and CH3) with 2- amino-3-(5-bromo-2-hydroxybenzylamino)maleonitrile. The solvatochromic behaviors of the molecules were probed by studying their UV–Vis spectra in five pure organic solvents of different polarities. The p-NO2 substituted receptor shows a dramatic color change from yellowto blue upon the addition of fluoride ion in CH3CN. This capability was studied by systematic TD-DFT calculations. These compounds were assayed for their in vitro antibacterial activities against Gram-positive (S. aureus, S. epidermidis and L. monocytogenes) and Gram-negative (E. coli, P. aeruginosa and K.pneumonia.) bacteria by disc diffusion method. The results indicated that the compounds show good inhibition against Gram positive bacteria namely L. monocytogenes as compared to standard drugs

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