5-arylidene-2,4-thiazolidinediones as inhibitors of protein tyrosine phosphatases

被引：106

作者：

Maccari, Rosanna ^{[1
]}

Paoli, Paolo

Ottana, Rosaria

Jacomelli, Michela

Ciurleo, Rosella

Manao, Giampaolo

Steindl, Theodora

Langer, Thierry

Vigorita, Maria Gabriella

Camici, Guido

机构：

[1] Univ Messina, Dipartimento Farmacochim, I-98168 Messina, Italy

[2] Univ Florence, Dipartimento Sci Biochim, I-50134 Florence, Italy

[3] Univ Innsbruck, Dept Pharmaceut Chem, Inst Pharm, A-6020 Innsbruck, Austria

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2007年 / 15卷 / 15期

关键词：

protein tyrosine phosphatases; diabetes mellitus; PTP1B and LMW-PTP inhibitors; molecular modelling;

D O I：

10.1016/j.bmc.2007.05.027

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

4-(5-Arylidene-2,4-dioxothiszolidin-3-yl)methylbenzoic acids (2) were synthesized and evaluated in vitro as inhibitors of PTP1B and LMW-PTP, two protein tyrosine phosphatases (PTPs) which act as negative regulators of the metabolic and mitotic signalling of insulin. The synthesis of compounds 2 represents an example of utilizing phosphotyrosine-mimetics to identify effective low molecular weight nonphosphorus inhibitors of PTPs. several thiazolidinediones 2 exhibited PTP1 B inhibitory activity in the low micromolar range with moderate selectivity for human PTP1B and IF1 isoform of human LMW-PTP compared with other related PTPs. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：5137 / 5149

页数：13

共 68 条

[1]

*ACC INC, 2005, CER REL 4 10

[2]

*ACC INC, 2005, CAT REL 4 10

[3] Protein tyrosine phosphatases in the human genome [J].

Alonso, A ;

Sasin, J ;

Bottini, N ;

Friedberg, I ;

Osterman, A ;

Godzik, A ;

Hunter, T ;

Dixon, J ;

Mustelin, T .

CELL, 2004, 117 (06) :699-711

[4] Discovery and SAR of a novel selective and orally bioavailable nonpeptide classical competitive inhibitor class of protein-tyrosine phosphatase 1B [J].

Andersen, HS ;

Olsen, OH ;

Iversen, LF ;

Sorensen, ALP ;

Mortensen, SB ;

Christensen, MS ;

Branner, S ;

Hansen, TK ;

Lau, JF ;

Jeppesen, L ;

Moran, EJ ;

Su, J ;

Bakir, F ;

Judge, L ;

Shahbaz, M ;

Collins, T ;

Vo, T ;

Newman, MJ ;

Ripka, WC ;

Moller, NPH .

JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (20) :4443-4459

[5] Small molecule peptidomimetics containing a novel phosphotyrosine bioisostere inhibit protein tyrosine phosphatase 1B and augment insulin actions [J].

Bleasdale, JE ;

Ogg, D ;

Palazuk, BJ ;

Jacob, CS ;

Swanson, ML ;

Wang, XY ;

Thompson, DP ;

Conradi, RA ;

Mathews, WR ;

Laborde, AL ;

Stuchly, CW ;

Heijbel, A ;

Bergdahl, K ;

Bannow, CA ;

Smith, CW ;

Svensson, C ;

Liljebris, C ;

Schostarez, HJ ;

May, PD ;

Stevens, FC ;

Larsen, SD .

BIOCHEMISTRY, 2001, 40 (19) :5642-5654

[6] Synthesis and aldose reductase inhibitory activity of 5-arylidene-2,4-thiazolidinediones [J].

Bruno, G ;

Costantino, L ;

Curinga, C ;

Maccari, R ;

Monforte, F ;

Nicolò, F ;

Ottanà, R ;

Vigorita, MG .

BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (04) :1077-1084

[7] Phosphotyrosyl mimetics in the development of signal transduction inhibitors [J].

Burke, TR ;

Lee, K .

ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (06) :426-433

[8] Coordinated action of protein tyrosine phosphatases in insulin signal transduction [J].

Cheng, A ;

Dubé, N ;

Gu, F ;

Tremblay, ML .

EUROPEAN JOURNAL OF BIOCHEMISTRY, 2002, 269 (04) :1050-1059

[9] LMW-PTP is a positive regulator of tumor onset and growth [J].

Chiarugi, P ;

Taddei, ML ;

Schiavone, N ;

Papucci, L ;

Giannoni, E ;

Fiaschi, T ;

Capaccioli, S ;

Raugei, G ;

Ramponi, G .

ONCOGENE, 2004, 23 (22) :3905-3914

[10] PDGF RECEPTOR AS A SPECIFIC IN-VIVO TARGET FOR LOW M(R) PHOSPHOTYROSINE PROTEIN PHOSPHATASE [J].

CHIARUGI, P ;

CIRRI, P ;

RAUGEI, G ;

CAMICI, G ;

DOLFI, F ;

BERTI, A ;

RAMPONI, G .

FEBS LETTERS, 1995, 372 (01) :49-53

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