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Abstract
In the present study, five 4-aminophenol derivatives (4-chloro-2-(((4-hydroxyphenyl)imino)methyl)phenol(S-1), 4-((4-(dimethylamino)benzylidene)amino)phenol(S-2), 4-((3-nitrobenzylidene)amino)phenol(S-3), 4-((thiophen-2-ylmethylene)amino)phenol(S-4) and 4-(((E)-3-phenylallylidene)amino)phenol(S-5)) were synthesized and characterized by FT-IR, 1H-NMR, 13C-NMR and elemental analyses. The synthesized compounds were tested for their antimicrobial (Gram-positive and Gram-negative bacteria and Saccharomyces cervesea fungus) and antidiabetic (α-amylase and α-glucosidase inhibitory) activities. All the compounds showed broad-spectrum activities against the Staphylococcus aureus (ATCC 6538), Micrococcus luteus (ATCC 4698), Staphylococcus epidermidis (ATCC 12228), Bacillus subtilis sub. sp spizizenii (ATCC 6633), Bordetella bronchiseptica (ATCC 4617) and Saccharomyces cerevisiae (ATCC 9763) strains. The newly synthesized compounds showed a significant inhibition of amylase (93.2%) and glucosidase (73.7%) in a concentration-dependent manner. Interaction studies of Human DNA with the synthesized Schiff bases were also performed. The spectral bands of S-1, S-2, S-3 and S-5 all showed hyperchromism, whereas the spectral band of S-4 showed a hypochromic effect. Moreover, the spectral bands of the S-2, S-3 and S-4 compounds were also found to exhibit a bathochromic shift (red shift). The present studies delineate broad-spectrum antimicrobial and antidiabetic activities of the synthesized compounds. Additionally, DNA interaction studies highlight the potential of synthetic compounds as anticancer agents. The DNA interaction studies, as well as the antidiabetic activities articulated by the molecular docking methods, showed the promising aspects of synthetic compounds.
Highlights
The sequential order to add the chemicals in the reaction mixture prepared in a 96-well plate was as follows: 25 μL of p-nitrophenyl β-D-glucopyranoside (p-NPG) (20 mM), 69 μL of phosphate buffer (50 mM, pH 6.8), 1 μL
The synthesized compounds were of different colors
The band at 1668 cm−1 that was assigned to ν(C=O) stretching in cinnamaldehyde was shifted to 1643 cm−1 for ν(C=N) azomethine group formation in the synthesized S-5 Schiff base
Summary
This paper presents a series of Schiff bases with a potential biological activity resulting from the acid-catalyzed condensation of aldehydes with aromatic amines. These compounds could act as valuable ligands. Schiff bases derived from heterocyclic rings present many advantages, and the most predominant heteroatoms found in organic molecules are mainly nitrogen (N), oxygen (O), and sulfur (S) [18] As it is genetic material and contains all cellular information, the study of DNA interaction is a very important aspect at present. The synthesized Schiff base derivatives were evaluated for their potential biological activities, i.e., antibacterial, antidiabetic and DNA interaction studies, etc
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