Unveiling the Antitubercular Potential of Furan–Nitrophenyl Schiff Base Hybrids: A Molecular Docking and Drug-Likeness Perspective

• Published in: Russian journal of general chemistry Vol. 94; no. 8; pp. 1997 - 2007
• Main Authors: Abdelwahab, G. A., Elmorsy, M. R., Fadda, A. A., Ismail, M. A.
• Format: Journal Article
• Language: English
• Published: Moscow Pleiades Publishing 01.08.2024; Springer Nature B.V
• Subjects: Binding; Chemical synthesis; Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Imines; Molecular docking; Reductases; Tuberculosis; furan-based Schiff bases; docking; antitubercular activity; Meerwein reaction; InhA; ADME
• ISSN: 1070-3632; 1608-3350
• DOI: 10.1134/S1070363224080139

In this study, we report the synthesis and characterization using various spectroscopic techniques of a series of six new furan-based Schiff base derivatives as potential antitubercular agents. The strategic incorporation of the furan scaffold and nitro group, both known for their diverse biological activities, provided a strong rationale for their evaluation against tuberculosis. Molecular docking simulations were employed to assess the binding affinities of these compounds towards enoyl-acyl carrier protein reductase (InhA), a validated and essential target in M. tuberculosis . Remarkably, all synthesized compounds exhibited superior binding scores (–6.074 to –9.939 kcal/mol), compared to the clinically used antitubercular drug isoniazid (–4.585 kcal/mol), indicating their potential as potent InhA inhibitors. Furthermore, in silico absorption, distribution, metabolism, and excretion (ADME) predictions were performed to evaluate the drug-likeness of these compounds. The findings highlight the balanced combination of potent target binding and drug-like characteristics achieved by these furan-based Schiff base hybrids.