Facile Syntheses and Studies of 8-Substituted-4-(4-tert-butylphenyl/ 4-acetamidophenyl)-2,3-dihydro-1,5-benzothiazepine-2-carboxylic Acids

Abstract

Two series of new 8-substituted-4-(4-tert-butylphenyl)-2,3-dihydro-1,5-benzothiazepine-2-carboxylic acids and 8-substituted-4-(4-acetamidophenyl)-2,3-dihydro-1,5-benzothiazepine-2-carboxylic acids have been synthesized by Michael condensation of 5-substituted-2-aminobenzenethiols with β-(4- tert-butylbenzoyl) acrylic acid or β-(4-acetamidobenzoyl) acrylic acid, in ethanol in acidic medium in a single step, in 58-64 % yield. The structures of the newly synthesized compounds were confirmed by their IR, 1H NMR and mass spectral analyses and micro analytical data. They were screened for antimicrobial activity, against the Gram-positive bacteria, Staphylococcus aureus, Gram-negative bacteria, Enterobacter cloacae and Escherichia coli, with respective reference compounds, vancomycin, polymyxin B, colistin-polymyxin B and against the fungus, Candida albicans with reference drug fluconazole. Most of the compounds showed activity against Staphylococcus aureus, Enterobacter cloacae and fungus Candida albicans, while none of the compounds showed activity against Escherichia coli.