Syntheses and Studies of 8-Substituted-2-(2-Chlorophenyl/3-chlorophenyl)- 4-(4-hydroxyphenyl/phenyl)-2,3/2,5-dihydro-1,5-benzothiazepines

Abstract

Syntheses of novel twelve 8-substituted-2-(2-chlorophenyl/3-chlorophenyl)-4-(4-hydroxyphenyl/ phenyl)-2,3/2,5-dihydro-1,5-benzothiazepines have been carried out by the reactions of 5-substituted 2-aminobenzenethiols, the substituents being fluoro, chloro, bromo, methyl, methoxy or ethoxy with α,β-unsaturated ketones, 3-(2-chlorophenyl)-1-(4-hydroxyphenyl)-2-propenone or 3-(3-chloro-phenyl)-1-phenyl-2-propenone in dry ethanol in acidic medium in quest for the synthesis of 1,5-benzothiazepine compounds, which may have interesting biological activities. The precursors, substituted α,β-unsaturated ketones were obtained by employing the Claisen-Schmidt reaction; and the final products, obtained by Michael condensation, were characterized by analytical and spectral data comprising IR, 1H NMR and mass spectral studies. Two different series, 2,3-dihydro and 2,5-dihydro series of the final compounds were obtained depending on the substituents present, as indicated by the 1H NMR spectra. The newly synthesized compounds were studied for their antimicrobial activities against Staphylococcus aureus, Escherichia coli and Candida albicans taking imipenem, vancomycin and fluconazole as reference standards using Paper Disc method. Five of the compounds tested showed good antifungal activity against Candida albicans at the concentration of 200 μg/disc.