Palladium-catalyzed N-arylation of 2-aminobenzothiazole-4-carboxylates/carboxamides: facile synthesis of PARP14 inhibitors

被引：13

作者：

Wang, Pingyuan ^{[1
]}

Li, Jian ^{[2
,3
]}

Jiang, Xue ^{[4
]}

Liu, Zhiqing ^{[2
,3
]}

Ye, Na ^{[2
,3
]}

Xu, Youjun ^{[4
]}

Yang, Guangfu ^{[1
]}

Xu, Yechun ^{[2
,3
]}

Zhang, Ao ^{[2
,3
]}

机构：

[1] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China

[2] Chinese Acad Sci, SIMM, CAS Key Lab Receptor Res, Shanghai 201203, Peoples R China

[3] Chinese Acad Sci, SIMM, State Key Lab Drug Res, Shanghai 201203, Peoples R China

[4] Shenyang Pharmaceut Univ, Sch Pharmaceut Engn, Shenyang 110000, Peoples R China

来源：

TETRAHEDRON | 2014年 / 70卷 / 35期

关键词：

2-Arylaminobenzothiazoles; PARP14; N-arylation; C-N coupling; Pd-2(dba)(3); S BOND FORMATION; TRANS-RETINOIC ACID; ONE-POT SYNTHESIS; TANDEM REACTION; ARYL HALIDES; INTRAMOLECULAR CYCLIZATION; COUPLING REACTIONS; SOLVENT-FREE; 2-AMINOBENZOTHIAZOLES; AMINATION;

D O I：

10.1016/j.tet.2014.06.064

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have developed a palladium-catalyzed N-arylation of the biologically interesting, but synthetically rather challenging 2-arylaminobenzothiazoles bearing multiple functionalities. This protocol was successfully used to readily synthesize our initial PARP14 inhibitor followed by a limited structural optimization. A more potent PARP14 inhibitor with an IC50 value of 1.69 mu M was identified, and the interaction was ascertained by the X-ray co-crystal structure of the catalytic domain of PARP14 in complex with compound 8. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：5666 / 5673

页数：8

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