Open AccessSyntheses and Studies of 8-Substituted-2-(2-Chlorophenyl/3-chlorophenyl)- 4-(4-hydroxyphenyl/phenyl)-2,3/2,5-dihydro-1,5-benzothiazepines
Author(s) -
Seema Pant,
Pushpa Godwal,
Kumari Sanju
Publication year - 2021
Publication title -
asian journal of chemistry/asian journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.145
H-Index - 34
eISSN - 0975-427X
pISSN - 0970-7077
DOI - 10.14233/ajchem.2021.23369
Subject(s) - chemistry , candida albicans , antimicrobial , alkoxy group , antifungal , proton nmr , fluconazole , ethanol , corpus albicans , carbon 13 nmr , stereochemistry , organic chemistry , medicinal chemistry , yeast , microbiology and biotechnology , biochemistry , alkyl , biology
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-substituted2-aminobenzenethiols, the substituents being fluoro, chloro, bromo, methyl, methoxy or ethoxywith α,β-unsaturated ketones, 3-(2-chlorophenyl)-1-(4-hydroxyphenyl)-2-propenone or3-(3-chloro-phenyl)-1-phenyl-2-propenone in dry ethanol in acidic medium in quest for the synthesisof 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; andthe final products, obtained by Michael condensation, were characterized by analytical and spectraldata comprising IR, 1H NMR and mass spectral studies. Two different series, 2,3-dihydro and2,5-dihydro series of the final compounds were obtained depending on the substituents present, asindicated by the 1H NMR spectra. The newly synthesized compounds were studied for their antimicrobialactivities against Staphylococcus aureus, Escherichia coli and Candida albicans taking imipenem,vancomycin and fluconazole as reference standards using Paper Disc method. Five of the compoundstested showed good antifungal activity against Candida albicans at the concentration of 200 μg/disc.