Syntheses of 1,5-benzothiazepines: Part XXXIII- Syntheses and antimicrobial studies of 10-substituted-6- (4-methoxyphenyl)- 6H-6a,7-dihydro-7- (4-methoxyphenyl/3,4- dimethoxyphenyl) [1]benzopyrano-[3,4-c][1,5] benzothiazepines

Abstract

Two flavindogenides, 2-(4-methoxyphenyl)-3-(4-methoxybenzylidene)- flavanone, 8a and 2-(4-methoxyphenyl)-3- (3,4-dimethoxybenzylidene)-flavanone 8b, are reacted with 5-substituted-2-aminobenzenethiols 3a-f (the substituents being halogens, fluoro, chloro or bromo, methyl and alkoxyls, methoxyl or ethoxyl), to give respective 12 new compounds, 10-substituted-6-(4-methoxyphenyl)-6H-6a, 7-dihydro-7-(4-methoxyphenyl/3,4- dimethoxyphenyl)[1]benzopyrano[3,4-c]- [1,5]benzothiazepines 10a-l in 55-67% yields. The products are characterized on the basis of analytical and spectral data. The synthesized compounds are screened for antimicrobial activity against the bacteria Staphylococcus aureus, Pseudo-monas aeruginosa, and the fungus Candida albicans. All the methoxy-substituted benzopyranobenzothiazepines have showed moderate to comparable activity (using gatifloxin, natilmicin as reference standard) against the gram-positive bacteria S. aureus and the gram-negative bacteria P. aeruginosa. They have also showed significant antifungal activity (compared to fluconazole) against C. albicans, the maximum activity being that of the compound 10k having maximum methoxyl groups, while the fluoro compounds 10a and 10g are completely inactive.