Novel diazepine derivatives of naphthofuran: synthesis, structural characterization, and biological assessment
Keywords:
Acetylnaphtho[2,1-b]furan, 1,5-benzodiazepines, Molecular docking, Antimicrobial activity, Minimum Inhibitory Concentration [MIC]Abstract
2-Hydroxy-1-naphthaldehyde (1) was reacted with chloroacetone and anhydrous K₂CO₃ in dry acetone to yield 2-acetylnaphtho[2,1-b]furan (2). Subsequent treatment of compound (2) with isatin, piperidine, and ethanol afforded the corresponding 2-(3′-hydroxy-2′-oxoindolyl)acetylnaphtho[2,1-b]furan (3), which upon dehydration produced the α,β-unsaturated ketones (4). Cyclocondensation of compound (4) with substituted o-phenylenediamines furnished a series of novel 4′-[naphtho[2,1-b]furan-2-yl]spiro[3H-indole-3,2′-1,5-benzodiazepine]-2(1H)-one derivatives (C1–C7).
Molecular docking studies were performed, and the best-scoring compounds were synthesized and structurally confirmed using IR, NMR, and mass spectral analyses. These derivatives were further evaluated for their antimicrobial activity using the MIC method.
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