Design and Synthesis of N -Sulfonylamidines of Modafinic Acid / Beryozkina T., Bakulev V., Dianova L., Berseneva V., Slepukhin P., Leban J., Kalaba P., Aher N.Y., Ilic M., Sitte H.H., Lubec G. // Synthesis (Germany). - 2016. - V. 48, l. 7. - P. 1046-1054.

ISSN:
00397881
Type:
Article
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. © Georg Thieme Verlag Stuttgart New York.
Author keywords:
azides; DAT inhibitors; modafinil; N -sulfonyl amidines; thioamides
Index keywords:
Amines; Neurophysiology; Nitrogen compounds; azides; Dopamine transporters; Modafinil; Oxidation of sulfides; Sulfonyl azides; Thioamides; Thionation; Two-product; Organic solvents
DOI:
10.1055/s-0035-1561350
Смотреть в Scopus:
https://www.scopus.com/inward/record.uri?eid=2-s2.0-84957600253&doi=10.1055%2fs-0035-1561350&partnerID=40&md5=3d2e64fba0147f21822b11fc757ea8a4
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Art. No. ss-2015-t0635-op
Link https://www.scopus.com/inward/record.uri?eid=2-s2.0-84957600253&doi=10.1055%2fs-0035-1561350&partnerID=40&md5=3d2e64fba0147f21822b11fc757ea8a4
Affiliations Ural Federal University Named after the First President of Russia B. N. Yeltsin 19 Mira St., Yekaterinburg, Russian Federation; I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of Russian Academy of Sciences, 20 S. Kovalevskaya st., Yekaterinburg, Russian Federation; Department of Pharmaceutical Chemistry, Faculty of Life Sciences, University of Vienna, Althanstrae 14, Vienna, Austria; Institute of Pharmacology, Center of Physiology and Pharmacology, Medical University of Vienna, Vienna, Austria
Author Keywords azides; DAT inhibitors; modafinil; N -sulfonyl amidines; thioamides
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Correspondence Address Bakulev, V.; Ural Federal University Named after the First President of Russia B. N. Yeltsin 19 Mira St.Russian Federation; email: v.a.bakulev@urfu.ru
Publisher Georg Thieme Verlag
CODEN SYNTB
Language of Original Document English
Abbreviated Source Title Synthesis
Source Scopus