Development of Benzo[b]thiophene Linked-Oxadiazole Derivatives for Potential Antimicrobial and Anti-TB Targets: Evaluation of ADME-Tox and In-silico Docking
Abstract
The present work reports the synthesis of new bis-oxadiazole-bearing benzo[b]thiophene derivatives as well as assessments of their antimicrobial and antitubercular activity through both in vitro and in silico approaches. The novel benzo[b]thiophene-based oxadiazole derivatives (7a−7k) were synthesized via a three-step path involving the preparation of thioacetonitrile, followed by the conversion to acetimidamide, and finally cyclization with various functionalized benzoic acids. The structural elucidation of the prepared benzo[b]thiophene compounds was established by ¹H-NMR, ¹³C-NMR, and HRMS spectroscopic analysis. In vitro antimicrobial activity against Gram-(–ve), Gram(+ve) and fungal microorganisms and antitubercular effect on the H37Rv strain were assessed for each synthesized compound. It was revealed that compound 7f showed well-established antibacterial affinities on S. aureus and P. aeruginosa with zones of inhibition of 39.95±0.82 and 37.29±0.33 mm in comparison to the reference drug gemifloxacin (37.02±0.92 and 36.10±2.17 mm). Notably, compounds 7c and 7h displayed the highest antifungal activity among the tested compounds, with selectivity towards the C. albicans ZI values of 30.15±0.28 and 31.37±1.32 mm, with respects to CLZ (ZI = 29.36±1.15 mm). Among them, oxadiazole conjugates 7a (MIC = 5.80 μM), 7f (2.89 μM), and 7h (3.10 μM) showed potent anti-TB activity on the tested H37Rv compared to the conventional drug STM. Moreover, in silico molecular docking…
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