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Fused thiochromeno[4,3-d]isoxazoles: One-pot synthesis, antibacterial, antibiofilim, and in silico studies

Journal of Molecular Structure, ISSN: 0022-2860, Vol: 1325
2025
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Article Description

In this study, we designed and synthesized several novel fused isoxazole derivatives using a single [3 + 2] reaction cycloaddition reaction of 4-((3-iodoprop-2-yn-1-yl)sulfonyl)-N,N-dimethylaniline followed by C-C bond coupling with various nitrile oxides in a PEG-400 under microwave conditions. Later, Minimum Inhibitory Concentration of the newly synthesized compounds (6a–6p) was determined against three G+ve bacterial strains, B. subtilis, S. aureus, and S. epidermidis. When compared to the reference molecule, dicloxacillin, the majority of the compounds demonstrated adequate efficacy. Among the compounds investigated, compounds 6f, 6g, 6h, 6j, and 6k demonstrated the most promising MIC values compared to others. The MIC values ranged from 1.56 µg to 12.5 µg, especially compounds 6f and 6k, which displayed superior activity against B. subtilis and S. aureus strains compared to the standard dicloxacillin. We also documented the results of anti-biofilm profiles for the compounds 6f, 6g, 6h, 6j, and 6k. Based on the result, we noted that, the active derivatives 6f and 6k strongly inhibited the biofilm of B. subtilis and S. aureus biofilm growth, with BFIC values ranging from 2.89 ± 0.21 µg/mL to 5.94 ± 0.32 (P<0.001) µg/mL. Our further aim is the time-kill studies of the human pathogenic organism using 6f and 6k compounds. Docking simulations also performed on the MRSA PBP2a (PDB: 1MWT) of more potent compounds consistently formed three hydrogen bond interactions with the active site residues SER598, HIS583, and SER643.

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