Design and synthesis of potent, non-peptidic inhibitors of HPTPβ

被引:34
作者
Amarasinghe, Kande K. D.
Evidokimov, Artem G.
Xu, Kevin
Clark, Cynthia M.
Maier, Matthew B.
Srivastava, Anil
Colson, Anny-Odile
Gerwe, Gina S.
Stake, George E.
Howard, Brian W.
Pokross, Matthew E.
Gray, Jeffrey L.
Peters, Kevin G.
机构
[1] Procter & Gamble Pharmaceut, Hlth Care Res Ctr, Mason, OH 45040 USA
[2] Chembiotek Res Inst, Kolkata 700091, W Bengal, India
关键词
protein tyrosine phosphatases; HPTP beta; sulfamic acid; malonates; oxadiazoles; PROTEIN-TYROSINE PHOSPHATASES; ENDOTHELIAL GROWTH-FACTOR; ANGIOPOIETIN-1;
D O I
10.1016/j.bmcl.2006.05.074
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The sulfamic acid phosphotyrosine mimetic was coupled with a previously known malonate template to obtain highly selective and potent inhibitors of HPTP beta. Potentially hydrolyzable malonate ester functionalities were replaced with 1,2,4-oxadiazoles without a significant effect on HPTP beta potency. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4252 / 4256
页数:5
相关论文
共 20 条
[1]   One-pot synthesis of 1,2,4-oxadiazoles from carboxylic acid esters and amidoximes using potassium carbonate [J].
Amarasinghe, Kande K. D. ;
Maier, Matthew B. ;
Srivastava, Anil ;
Gray, Jeffrey L. .
TETRAHEDRON LETTERS, 2006, 47 (22) :3629-3631
[2]   Inhibitors of protein tyrosine phosphatases: Next-generation drugs? [J].
Bialy, L ;
Waldmann, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (25) :3814-3839
[3]  
Blaskovich MA, 2002, EXPERT OPIN THER PAT, V12, P871
[4]   Signaling and functions of angiopoietin-1 in vascular protection [J].
Brindle, NPJ ;
Saharinen, P ;
Alitalo, K .
CIRCULATION RESEARCH, 2006, 98 (08) :1014-1023
[5]   Tyrosine phosphatase inhibition augments collateral blood flow in a rat model of peripheral vascular disease [J].
Carr, AN ;
Davis, MG ;
Eby-Wilkens, E ;
Howard, BW ;
Towne, BA ;
Dufresne, TE ;
Peters, KG .
AMERICAN JOURNAL OF PHYSIOLOGY-HEART AND CIRCULATORY PHYSIOLOGY, 2004, 287 (01) :H268-H276
[6]   Coadministration of angiopoietin-1 and vascular endothelial growth factor enhances collateral vascularization [J].
Chae, JK ;
Kim, I ;
Lim, ST ;
Chung, MJ ;
Kim, WH ;
Kim, HG ;
Ko, JK ;
Koh, GY .
ARTERIOSCLEROSIS THROMBOSIS AND VASCULAR BIOLOGY, 2000, 20 (12) :2573-2578
[7]   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
[8]   PTP-1B inhibitors:: Cyclopenta[d][1,2]-oxazine derivatives [J].
Cho, SY ;
Baek, JY ;
Han, SS ;
Kang, SK ;
Ha, JD ;
Ahn, JH ;
Lee, JD ;
Kim, KR ;
Cheon, HG ;
Rhee, SD ;
Yang, SD ;
Yon, GH ;
Pak, CS ;
Choi, JK .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (03) :499-502
[9]   Functional interaction of vascular endothelial-protein-tyrosine phosphatase with the Angiopoietin receptor Tie-2 [J].
Fachinger, G ;
Deutsch, U ;
Risau, W .
ONCOGENE, 1999, 18 (43) :5948-5953
[10]   Growth factors acting via endothelial cell-specific receptor tyrosine kinases: VEGFs, angiopoietins, and ephrins in vascular development [J].
Gale, NW ;
Yancopoulos, GD .
GENES & DEVELOPMENT, 1999, 13 (09) :1055-1066