Synthesis and biological evaluation of diastereomeric (E and Z) sulfides, sulfones, sulfide-sulfones, and disulfones

摘要

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. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.