Isoxazole carboxylic acids as protein tyrosine phosphatase 1B (PTP1B) inhibitors

被引：84

作者：

Zhao, HY ^{[1
]}

Liu, G

Xin, ZL

Serby, MD

Pei, ZH

Szczepankiewicz, BG

Hajduk, PJ

Abad-Zapatero, C

Hutchins, CW

Lubben, TH

Ballaron, SJ

Haasch, DL

Kaszubska, W

Rondinone, CM

Trevillyan, JM

Jirousek, MR

机构：

[1] Abbott Labs, Global Pharmaceut Res & Dev, Metab Dis Res, Abbott Pk, IL 60064 USA

[2] Abbott Labs, Global Pharmaceut Res & Dev, Adv Technol, Abbott Pk, IL 60064 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2004年 / 14卷 / 22期

关键词：

PTP1B; selective; cell permeable;

D O I：

10.1016/j.bmcl.2004.08.063

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Guided by X-ray crystallography, we have extended the structure-activity relationship (SAR) study on an isoxazole carboxylic acid-based PTP1B inhibitor (1) and more potent and equally selective (>20-fold selectivity over the highly homologous T-cell PTPase, TCPTP) PTP1B inhibitors were identified. Inhibitor 7 demonstrated good cellular activity against PTP1B in COS 7 cells. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：5543 / 5546

页数：4

共 25 条

[1] CRYSTAL-STRUCTURE OF HUMAN PROTEIN-TYROSINE-PHOSPHATASE 1B [J].

BARFORD, D ;

FLINT, AJ ;

TONKS, NK .

SCIENCE, 1994, 263 (5152) :1397-1404

[2] 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

[3] Increased insulin sensitivity and obesity resistance in mice lacking the protein tyrosine phosphatase-1B gene [J].

Elchebly, M ;

Payette, P ;

Michaliszyn, E ;

Cromlish, W ;

Collins, S ;

Loy, AL ;

Normandin, D ;

Cheng, A ;

Himms-Hagen, J ;

Chan, CC ;

Ramachandran, C ;

Gresser, MJ ;

Tremblay, ML ;

Kennedy, BP .

SCIENCE, 1999, 283 (5407) :1544-1548

[4] The T-cell protein tyrosine phosphatase [J].

Ibarra-Sánchez, MD ;

Simoncic, PD ;

Nestel, FR ;

Duplay, P ;

Lapp, WS ;

Tremblay, ML .

SEMINARS IN IMMUNOLOGY, 2000, 12 (04) :379-386

[5] Protein tyrosine phosphatase 1B inhibitors for diabetes [J].

Johnson, TO ;

Ermolieff, J ;

Jirousek, MR .

NATURE REVIEWS DRUG DISCOVERY, 2002, 1 (09) :696-709

[6] PREPARATION OF IODOALLYLIC ALCOHOLS VIA HYDROSTANNYLATION - SPECTROSCOPIC PROOF OF STRUCTURES [J].

JUNG, ME ;

LIGHT, LA .

TETRAHEDRON LETTERS, 1982, 23 (38) :3851-3854

[7] Protein tyrosine phosphatase 1B negatively regulates leptin signaling in a hypothalamic cell line [J].

Kaszubska, W ;

Falls, HD ;

Schaefer, VG ;

Haasch, D ;

Frost, L ;

Hessler, P ;

Kroeger, PE ;

White, DW ;

Jirousek, MR ;

Trevillyan, JM .

MOLECULAR AND CELLULAR ENDOCRINOLOGY, 2002, 195 (1-2) :109-118

[8] 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

[9] Modification of the N-terminus of peptidomimetic protein tyrosine phosphatase 1B (PTP1B) inhibitors: Identification of analogues with cellular activity [J].

Larsen, SD ;

Stevens, FC ;

Lindberg, TJ ;

Bodnar, PM ;

O'Sullivan, TJ ;

Schostarez, HJ ;

Palazuk, BJ ;

Bleasdale, JE .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (05) :971-975

[10] REACTIONS OF DILITHIO-NITROALKANES AND DILITHIO-ALLYLNITROALKANES WITH CARBONYL-COMPOUNDS [J].

LEHR, F ;

GONNERMANN, J ;

SEEBACH, D .

HELVETICA CHIMICA ACTA, 1979, 62 (07) :2258-2275

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