Design and synthesis of N-benzimidazol-2-yl-N'-sulfonyl acetamidines / Rupakova N.A., Bakulev V.A., Knippschild U., García-Reyes B., Eltsov O.S., Slesarev G.P., Beliaev N., Slepukhin P.A., Witt L., Peifer C., Beryozkina T.V. // Arkivoc. - 2017. - V. 2017, l. 3. - P. 225-240.

ISSN:

15517004

Type:

Article

Abstract:

N-Sulfonyl-N'-benzimidazol-2-yl acetamidines have been designed as CK1 inhibitors. Binding modes in the ATP pocket of CK1 were determined by molecular modeling. The synthetic approach involves sequential acylation of 2-aminobenzimidazoles followed by reaction of amides with Lawesson’s reagent and iminosulfonylation of thioamides with sulfonyl azides. The iminosulfonylation was carried out in boiling ethanol with an equivalent ratio of azides and thioamides. The synthesized compounds were tested for their ability to inhibit CK1 isoforms in vitro and to inhibit the growth of tumor cell lines. Among the synthesized compounds, two products showed inhibitory abilities towards CK1δ and CK1ε. ©ARKAT USA, Inc

Author keywords:

1; 3-dipolar cycloaddition; Benzimidazoles; CK1 inhibitors; N-sulfonyl amidines; Thioamides

Index keywords:

нет данных

DOI:

10.24820/ark.5550190.p010.200

Смотреть в Scopus:

https://www.scopus.com/inward/record.uri?eid=2-s2.0-85026846505&doi=10.24820%2fark.5550190.p010.200&partnerID=40&md5=2540567a4f941b0d61965e81b39bb20b

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Link	https://www.scopus.com/inward/record.uri?eid=2-s2.0-85026846505&doi=10.24820%2fark.5550190.p010.200&partnerID=40&md5=2540567a4f941b0d61965e81b39bb20b
Affiliations	Ural Federal University, 19 Mira st., Yekaterinburg, Russian Federation; Klinik für Allgemein- und Viszeralchirurgie Zentrum für Chirurgie Universitätsklinikum Ulm, 23 Albert-Einstein-Allee, Ulm, Germany; I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of Russian Academy of Sciences, 20 S. Kovalevskaya st., Yekaterinburg, Russian Federation; Institute of Pharmacy, Christian-Albrechts-University, Gutenbergstrasse 76, Kiel, Germany
Author Keywords	1; 3-dipolar cycloaddition; Benzimidazoles; CK1 inhibitors; N-sulfonyl amidines; Thioamides
Funding Details	17-03-00641, RFBR, Russian Foundation for Basic Research
Funding Text	We gratefully acknowledge financial support of this work by the Russian Foundation for Basic Research (project 17-03-00641). B.G.R. was kindly supported by the German Academic Exchange Service (DAAD). We also thank Marie-Therese Bammert for her technical support
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Correspondence Address	Beryozkina, T.V.; Ural Federal University, 19 Mira st., Russian Federation; email: tetber@mail.ru
Publisher	Arkat
CODEN	AGFUA
Language of Original Document	English
Abbreviated Source Title	Arkivoc
Source	Scopus