Synthesis, Inhaltsverzeichnis

Synthesis 2016; 48(07): 1046-1054
DOI: 10.1055/s-0035-1561350

paper

© Georg Thieme Verlag Stuttgart · New York

Design and Synthesis of N-Sulfonylamidines of Modafinic Acid

Tetyana Beryozkina

^aUral Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira st., 620002 Yekaterinburg, Russian Federation eMail: v.a.bakulev@urfu.ru

,

Vasiliy Bakulev*

^aUral Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira st., 620002 Yekaterinburg, Russian Federation eMail: v.a.bakulev@urfu.ru

,

Lidia Dianova

^aUral Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira st., 620002 Yekaterinburg, Russian Federation eMail: v.a.bakulev@urfu.ru

,

Vera Berseneva

^aUral Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira st., 620002 Yekaterinburg, Russian Federation eMail: v.a.bakulev@urfu.ru

,

Pavel Slepukhin

^aUral Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira st., 620002 Yekaterinburg, Russian Federation eMail: v.a.bakulev@urfu.ru

^bI. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of Russian Academy of Sciences, 20 S. Kovalevskaya st., 620990 Yekaterinburg, Russian Federation

,

Johann Leban

^cDepartment of Pharmaceutical Chemistry, Faculty of Life Sciences, University of Vienna, Althanstraße 14, 1090 Vienna, Austria

,

Predrag Kalaba

^cDepartment of Pharmaceutical Chemistry, Faculty of Life Sciences, University of Vienna, Althanstraße 14, 1090 Vienna, Austria

,

Nilima Yogesh Aher

^cDepartment of Pharmaceutical Chemistry, Faculty of Life Sciences, University of Vienna, Althanstraße 14, 1090 Vienna, Austria

,

Marija Ilic

^cDepartment of Pharmaceutical Chemistry, Faculty of Life Sciences, University of Vienna, Althanstraße 14, 1090 Vienna, Austria

,

Harald H. Sitte

^dInstitute of Pharmacology, Center of Physiology and Pharmacology, Medical University of Vienna, 1090 Vienna, Austria

,

Gert Lubec*

^cDepartment of Pharmaceutical Chemistry, Faculty of Life Sciences, University of Vienna, Althanstraße 14, 1090 Vienna, Austria

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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

Key words

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

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