Design and Synthesis of N-Sulfonylamidines of Modafinic Acid

Abstract

A design and a convenient approach for the synthesis of novel N-sulfonyl-2-diphenylmethylsulfinylacetamidines have been demonstrated by starting from benzhydrylsulfanylacetic (BSA) acid. This approach involves a sequential amidation with amines, thionation with Lawesson’s reagent, iminosulfonylation with sulfonyl azides, and oxidation of sulfide fragment with hydrogen peroxide. The key step of this transformation (reaction of thioamides with sulfonyl azides) was carried out either in ethanol or in the absence of any solvent. The synthesized compounds were tested in cells for inhibition of dopamine transporter. Among the synthesized compounds, two products were found to be in a similar range of activity as the well-known dopamine transporter inhibitor, modafinil.

Key words

modafinil - DAT inhibitors - N-sulfonyl amidines - azides - thioamides

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