Design and synthesis of N-benzimidazol-2-yl-N'-sulfonyl acetamidines / Rupakova Nadezhda A.,Bakulev Vasiliy A.,Knippschild Uwe,Garcia-Reyes Balbina,Eltsov Oleg S.,Slesarev Grigoriy P.,Beliaev Nikolai,Slepukhin Pavel A.,Witt Lydia,Peifer Christian,Beryozkina Tetyana V. // ARKIVOC. - 2017. - V. , l. 3. - P. 225-240.

ISSN/EISSN:

1551-7004 / 1551-7012

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 CK1 delta and CK1 epsilon.

Author keywords:

Thioamides; N-sulfonyl amidines; benzimidazoles; 1,3-dipolar cycloaddition; CK1 inhibitors CASEIN KINASE 1; POTENT INHIBITORS; SULFONYL AZIDES; PROTEIN; CK1-DELTA; EPSILON; P53; PHOSPHORYLATION; 1,2,3-TRIAZOLES; BENZIMIDAZOLES

DOI:

10.24820/ark.5550190.p010.200

Web of Science ID:

ISI:000408556800020

Соавторы в МНС:

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Другие поля

Поле	Значение
Publisher	ARKAT USA INC
Address	C/O ALAN R KATRITZKY, UNIV FLORIDA, DEPT CHEMISTRY, PO BOX 117200, GAINESVILLE, FL 32611 USA
Language	English
EISSN	1551-7012
Keywords-Plus	CASEIN KINASE 1; POTENT INHIBITORS; SULFONYL AZIDES; PROTEIN; CK1-DELTA; EPSILON; P53; PHOSPHORYLATION; 1,2,3-TRIAZOLES; BENZIMIDAZOLES
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	tetber@mail.ru
Funding-Acknowledgement	Russian Foundation for Basic Research {[}17-03-00641]; German Academic Exchange Service (DAAD)
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.
Number-of-Cited-References	37
Usage-Count-Last-180-days	3
Usage-Count-Since-2013	3
Journal-ISO	Arkivoc
Doc-Delivery-Number	FE9XM