Design and synthesis of N-benzimidazol-2-yl-N'-sulfonyl acetamidines

被引：12

作者：

Rupakova, Nadezhda A. ^{[1
]}

Bakulev, Vasiliy A. ^{[1
]}

Knippschild, Uwe ^{[2
]}

Garcia-Reyes, Balbina ^{[2
]}

Eltsov, Oleg S. ^{[1
]}

Slesarev, Grigoriy P. ^{[1
]}

Beliaev, Nikolai ^{[1
]}

Slepukhin, Pavel A. ^{[3
]}

Witt, Lydia ^{[4
]}

Peifer, Christian ^{[4
]}

Beryozkina, Tetyana V. ^{[1
]}

机构：

[1] Ural Fed Univ, 19 Mira St, Ekaterinburg 620002, Russia

[2] Univ Klinikum Ulm, Zentrum Chirurg, Klin Allgemein & Viszeralchirurg, 23 Albert Einstein Allee, D-89081 Ulm, Germany

[3] Russian Acad Sci, Ural Branch, I Ya Postovsky Inst Organ Synth, 20 S Kovalevskaya St, Ekaterinburg 620990, Russia

[4] Univ Kiel, Inst Pharm, Gutenbergstr 76, D-24118 Kiel, Germany

来源：

ARKIVOC | 2017年

基金：

俄罗斯基础研究基金会;

关键词：

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;

D O I：

10.24820/ark.5550190.p010.200

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：225 / 240

页数：16

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