Antitubercolusic Potential of Amino-(formylphenyl) Diazenyl-Hydroxyl and Nitro-Substituted Naphthalene-Sulfonic Acid Derivatives: Experimental and Theoretical Investigations

Tuberculosis (TB) is a long-term infection caused by the bacteria Mycobacterium tuberculosis, which continues to kill more people each year than any other infectious illness due to ineffective therapeutic agents for it. To help curb this trend and provide an alternative, this study aims to synthesize derivatives of diazenyl based organic compounds by diazotization of p-aminobenzaldehyde as the starting material for the four molecules. The compounds were characterized experimentally using FT-IR and UV spectroscopic techniques. In addition to understanding the vibrational energy distribution analysis (VEDA), Non-linear optics (NLO), Natural bond orbitals (NBO), Frontier molecular orbitals (FMO), the density of state (DOS), molecular electrostatic potential (MESP), Hirshfeld charges, and Fukui function were analyzed with DFT at B3LYP/6-31++G(d,p) level of theory. The results obtained from FMO indicated that the energy gap ranged from 6.169 to 7.042 eV. The global hardness for the compounds ranged from 2.648 to 3.327 eV. Whereas, the NBO interactions between sigma*C3-C4 -> pi*C1 - N20 with the stabilization energies of natural bond orbitals of 47,120.45 k/cal/mol for AZDH2. AZDH1 is examined to possess the lowest polarizability anisotropies (total) at - 203.57, while AZDH2 has the highest at - 151.59. Comprehensively, AZDH1 and AZDH2 elucidated great anti-antituberculosis potentials after analysing the molecular docking results.

Automated summary

This study aims to synthesize derivatives of diazenyl based organic compounds as an alternative treatment for tuberculosis. Experimental characterization and analysis of properties such as energy gap, hardness, NBO interactions, and polarizability revealed that certain compounds have strong anti-tuberculosis potential.