Synthesis and characterization of aniline‐based azo molecules: In vitro pharmacological and emission studies

• Published in: Luminescence (Chichester, England) Vol. 39; no. 10; pp. e4904 - n/a
• Main Authors: Shakuntala, R. B., Keshavayya, J., Mussuvir pasha, K. M., Pampapathi, S.
• Format: Journal Article
• Language: English
• Published: England Wiley Subscription Services, Inc 01-10-2024
• Subjects: 4‐hydroxy coumarin; Absorption spectra; Amines; Aniline; Aniline Compounds - chemical synthesis; Aniline Compounds - chemistry; Aniline Compounds - pharmacology; Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - pharmacology; Antibiotics; Antifungal Agents - chemical synthesis; Antifungal Agents - chemistry; Antifungal Agents - pharmacology; anti‐bacterial; Azo compounds; Azo Compounds - chemical synthesis; Azo Compounds - chemistry; Azo Compounds - pharmacology; Azo dyes; azo molecules; Chemical synthesis; Coupling (molecular); Density Functional Theory; Dyes; Fluorescence; Fourier transforms; Mass spectrometry; Mass spectroscopy; Microbial Sensitivity Tests; Microorganisms; Molecular docking; Molecular Docking Simulation; Molecular Structure; Mycobacterium tuberculosis - drug effects; NMR; Nuclear magnetic resonance; RDG plots; Room temperature; Sensitivity analysis; Spectra; Spectral methods; Spectrometry, Fluorescence; Tuberculosis; anti‐bacterial; RDG plots; azo molecules; 4‐hydroxy coumarin
• ISSN: 1522-7235; 1522-7243; 1522-7243
• DOI: 10.1002/bio.4904

The present work involves the synthesis of novel dispersed mono‐azo dyes using different coupling components and 2‐methoxy‐5‐nitro aniline as amine through a simple and convenient diazo‐coupling method. The structures of the newly synthesized mono azo dyes were confirmed by using various spectral techniques such as 1H NMR, Fourier transform infrared, and high‐resolution mass spectrometry. At room temperature, the electronic absorption spectra and fluorescence spectra of the synthesized mono azo dyes were recorded with different solvents. The global reactive parameters for the synthesized azo molecules were evaluated by performing density functional theory through the 6–311++G (d, p) basis set. The anti‐microbial activities for the synthesized azo compounds were carried out, and the compounds G1 and G2 exhibited good antibacterial and anti‐fungal activities. The in silico molecular docking studies of the azo molecules revealed that all the compounds exhibited extraordinary binding affinity as that of the standard drug. Further, the anti‐tuberculosis study against the Mycobacterium tuberculosis for the synthesized azo dyes was evaluated, and from the results, it was revealed that the compound G4 showed good sensitivity among the other synthesized azo compounds.
The aniline‐based azo dyes have synthesized by simple diazotization method under suitable laboratory conditions. The synthesized azo dyes derived from anilines have been confirmed by spectroscopic techniques. Further, these synthesized azo molecules have been evaluated for their biological activities such as anti‐microbial, anti‐tuberculosis, and in silico molecular docking.