A rapid synthesis of 2-((2-amino-4,6-dimethylpyrimidine-5yl)diazenyl)benzoic acid: Experimental, DFT study and DNA cleavage activity

Abstract

The newly synthesized 2-((2-amino-4,6-dimethylpyrimidine-5yl)diazenyl)benzoic acid has been prepared by diazotization of anthranilic acid and coupling with 2-amino-4,6-dimethylpyrimidine. Its structure has been characterized by spectroscopic measurements (1H NMR spectra, FT-IR spectra, mass spectra and UV–visible spectra) and thermal analysis technique. The DNA cleavage activity of compound is evaluated by agarose gel electrophoresis with a series of concentrations. Our measurements show that neither a disruptive effect created by 2-((2-amino-4,6-dimethylpyrimidine-5yl)diazenyl)benzoic acid on pBR 322 DNA are observed, nor the dependence of the concentration on the activity of newly synthetized chemical on pBR 322 plasmid DNA such as cleavage or break DNA double helix structure. Moreover, computational chemistry method based on Density Functional Theory (DFT) employing B3LYP level with 6-31G(d) basis set has been used to study geometry and spectroscopic properties such as FT-IR and UV–vis spectra of the titled compound considered in this work. The computations of the chemical shifts for 1H NMR of the title compound have been carried out via Gauge-Invariant Atomic Orbital (GIAO) method utilizing the same basis set. It is observed that DFT results are compatible with the experimental results. © 2018 Elsevier B.V.