Synthesis and Biological Evaluation of Diastereomeric (E and Z) Sulfides, Sulfones, Sulfide-Sulfones, and Disulfones

Abstract

The addition of p-chlorobenzenethiol to benzyl p-chlorophenylketone resulted in the formation of a mixture of diastereomers (E)- and (Z)-1-p-chlorophenyl-2-phenyl-1-p-chlorophenylthioethylene (1 and 2). These compounds, upon reaction with bromine in acetic acid, yielded a mixture of (E)- and (Z)-1-bromo-2-p-chlorophenyl-1-phenyl-2-p-chlorophenylthioethylenes (5a and 5b). Oxidation of 5a and 5b affords (E)- and (Z)-1-bromo-2-p-chlorophenyl-1-phenyl-2-p-chlorophenylsulfonylethylenes (6a and 6b), which upon reaction with the p-chlorobenzenethiol gave (E)- and (Z)-1-p-chlorophenyl-1-p-chlorophenylsulfonyl-2-phenyl-2-p-chlorophenylthioethylenes (7a and 7b). Oxidation of 7a and 7b yielded (E)- and (Z)-1,2-bis(p-chlorophenylsulfonyl)-2-phenyl-1-p-chlorophenylethylenes (8a and 8b). The final products, 8a and 8b, were also synthesized from a mixture of diastereomers, (E)- and (Z)-2-p-chlorophenyl-1-phenyl-1-p-chlorophenylthioethylenes (3 and 4), yielding the intermediates 9a and 9b, 10a and 10b, and 11a and 11b. The configurations of these compounds were established by elemental analysis, IR, ¹H NMR, and mass spectra, and by their preparation from the

corresponding phenylketones and p-chlorophenylphenylacetylene. All these new compounds exhibited pronounced in vitro antibacterial and antifungal activities.

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GRAPHICAL ABSTRACT

Keywords:

• Antimicrobial activity
• disulfones
• (E)- and (Z)-isomers, sulfide-sulfones
• sulfides
• sulfones

Acknowledgments

The authors are thankful to the University Grants Commission, New Delhi, for financial help.