Design and Synthesis of N-Sulfonylamidines of Modafinic Acid / Beryozkina Tetyana,Bakulev Vasiliy,Dianova Lidia,Berseneva Vera,Slepukhin Pavel,Leban Johann,Kalaba Predrag,Aher Nilima Yogesh,Ilic Marija,Sitte Harald H.,Lubec Gert // SYNTHESIS-STUTTGART. - 2016. - V. 48, l. 7. - P. 1046-1054.

ISSN/EISSN:

0039-7881 / 1437-210X

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.

Author keywords:

modafinil; DAT inhibitors; N-sulfonyl amidines; azides; thioamides ORGANOPHOSPHORUS COMPOUNDS; MONOAMINE TRANSPORTERS; AMIDES; HETEROCYCLES; THIOAMIDES; REAGENTS; ANALOGS

DOI:

10.1055/s-0035-1561350

Web of Science ID:

ISI:000372882200014

Соавторы в МНС:

Другие поля

Поле	Значение
Month	APR
Publisher	GEORG THIEME VERLAG KG
Address	RUDIGERSTR 14, D-70469 STUTTGART, GERMANY
Language	English
EISSN	1437-210X
Keywords-Plus	ORGANOPHOSPHORUS COMPOUNDS; MONOAMINE TRANSPORTERS; AMIDES; HETEROCYCLES; THIOAMIDES; REAGENTS; ANALOGS
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	v.a.bakulev@urfu.ru
Funding-Acknowledgement	Russian Scientific Foundation {[}15-13-10031]
Funding-Text	This project was supported by the Russian Scientific Foundation (15-13-10031).
Number-of-Cited-References	29
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	6
Journal-ISO	Synthesis
Doc-Delivery-Number	DH6DW