Synthesis, Crystal Structure, Antibacterial and Antituberculosis Activities of Novel Thieno[2,3-b][1,4] dithiine-1,1-dioxide Derivatives

Abstract

A new thieno[2,3-b][1,4]dithiine-1,1-dioxide was prepared via intramolecular cycloaddition reaction between methyl β-sulfonyl ester of thiophene and  carbon disulfide (CS₂) or ethoxycabonyl isothiocyanate. A new compound methyl 2-((2,5-dichlorothiophen-3-yl)sulfonyl) acetate as  methyl β-sulfonyl ester was prepared via interaction between methyl 2-bromoacetate and sodium 2,5-dichlorothiophene-3-sulfinate, which utilized in the cycloaddition reactions. Compounds 17 and 19b were tested for their antibacterial activity against Staphylococcus aureus and Escherichia coli. Additionally, 17 and 19b were assessed for their antibacterial activity against Mycobacterium tuberculosis strain mc²6230. The tested compounds have shown insignificant activities toward the tested bacteria (minimal inhibitory concentration > 100 μM).