Synthesis, Solvatochromic, LFPs, Computational, and Electrochemical Investigation of Novel Sulfadiazine Azo Dyes and Their Biological Studies

The present work describes synthesis of azo dyes, spectroscopic data confirms the structures of the compounds (D1-D4). DFT, docking, Cyclic Voltammetry, and their α-Glucosidase inhibitory activity providing additional support.

Abstract

In this work, the four azo dyes (D1–D4) were synthesized from sulfadiazine with four different coupling components by diazo-coupling reaction at 0–5 °C. These synthesized azo colorants were confirmed by various spectroscopic techniques viz, FT-IR, LC–MS, ¹H NMR, and ¹³C NMR spectra. The electronic absorption and fluorescence spectra were recorded at room temperature with various solvents. The DFT studies have been employed using Gaussian 09 software with B3LYP/6–31 + G(d,p) basis set at the gaseous phase to calculate global reactive parameters. The electrochemical behavior of compounds is studied using cyclic voltammetry and results are employed to calculate HOMO and LUMO experimentally. The anticancer activity of prepared azo dyes exhibited that D3 has excellent anticancer properties (IC₅₀ = 44.3 µg/mL) as compared to reference standard doxorubicin. These findings were further supported by in silico molecular docking studies, which provide additional support to the compounds as an inhibitor of human breast cancer. The compound D3 was used to investigate the latent fingerprints on a non-porous surface. By the obtained results it can be claimed that azo dye derivatives could serve as lead compounds for the design and development of new scaffolds with industrial collaboration.

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