Synthesis of substituted bis(heteroaryl)maleimides

被引：65

作者：

Dubernet, M ^{[1
]}

Caubert, V ^{[1
]}

Guillard, J ^{[1
]}

Viaud-Massuard, MC ^{[1
]}

机构：

[1] UFR Sci Pharmaceut, Chim Organ Lab, SPOT, EA 3857, F-37200 Tours, France

来源：

TETRAHEDRON | 2005年 / 61卷 / 19期

关键词：

bis(heteroaryl)maleimides; Suzuki cross-coupling;

D O I：

10.1016/j.tet.2005.03.016

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Substituted bis(fur-2-yl), bis(fur-3-yl) and bis(thien-2-yl) maleimides with potential antidiabetic properties are described. Their synthesis involves, as a key step, a Suzuki cross-coupling between various boron derivatives and the diiodomaleimides. Therefore, a wide range of substituted symmetric and non-symmetric maleimide derivatives can be prepared. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：4585 / 4593

页数：9

共 30 条

[11] A new, efficient method for the synthesis of bisindolylmaleimides [J].

Faul, MM ;

Winneroski, LL ;

Krumrich, CA .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (17) :6053-6058

[12] One pot biaryl synthesis via in situ boronate formation [J].

Giroux, A ;

Han, YX ;

Prasit, P .

TETRAHEDRON LETTERS, 1997, 38 (22) :3841-3844

[13] Synthesis of new melatonin analogues from dimers of azaindole and indole by use of Suzuki homocoupling [J].

Guillard, J ;

Larraya, C ;

Viaud-Massuard, MC .

HETEROCYCLES, 2003, 60 (04) :865-877

[14] Probing the molecular basis for potent and selective protein-tyrosine phosphatase 1B inhibition [J].

Guo, XL ;

Kui, S ;

Wang, F ;

Lawrence, DS ;

Zhang, ZY .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2002, 277 (43) :41014-41022

[15] PALLADIUM(O)-CATALYZED CROSS-COUPLING REACTION OF ALKOXYDIBORON WITH HALOARENES - A DIRECT PROCEDURE FOR ARYLBORONIC ESTERS [J].

ISHIYAMA, T ;

MURATA, M ;

MIYAURA, N .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (23) :7508-7510

[16] Increased energy expenditure, decreased adiposity, and tissue-specific insulin sensitivity in protein-tyrosine phosphatase 1B-deficient mice [J].

Klaman, LD ;

Boss, O ;

Peroni, OD ;

Kim, JK ;

Martino, JL ;

Zabolotny, JM ;

Moghal, N ;

Lubkin, M ;

Kim, YB ;

Sharpe, AH ;

Stricker-Krongrad, A ;

Shulman, GI ;

Neel, BG ;

Kahn, BB .

MOLECULAR AND CELLULAR BIOLOGY, 2000, 20 (15) :5479-5489

[17] Protein tyrosine phosphatase 1B inhibition: Opportunities and challenges [J].

Liu, G .

CURRENT MEDICINAL CHEMISTRY, 2003, 10 (15) :1407-1421

[18] Selective protein tyrosine phosphatase 1B inhibitors: Targeting the second phosphotyrosine binding site with non-carboxylic acid-containing ligands [J].

Liu, G ;

Xin, ZL ;

Liang, H ;

Abad-Zapatero, C ;

Hajduk, PJ ;

Janowick, DA ;

Szczepankiewicz, BG ;

Pei, ZH ;

Hutchins, CW ;

Ballaron, SJ ;

Stashko, MA ;

Lubben, TH ;

Berg, CE ;

Rondinone, CM ;

Trevillyan, JM ;

Jirousek, MR .

JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (16) :3437-3440

[19] Fragment screening and assembly: A highly efficient approach to a selective and cell active protein tyrosine phosphatase 1B inhibitor [J].

Liu, G ;

Xin, ZL ;

Pei, ZG ;

Hajduk, PJ ;

Abad-Zapatero, C ;

Hutchins, CW ;

Zhao, HY ;

Lubben, TH ;

Ballaron, SJ ;

Haasch, DL ;

Kaszubska, W ;

Rondinone, CM ;

Trevillyan, JM ;

Jirousek, MR .

JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (20) :4232-4235

[20]

Liu Gang, 2002, Curr Opin Investig Drugs, V3, P1608

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