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

被引:33
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
    Amarasinghe, Kande K. D.
    Maier, Matthew B.
    Srivastava, Anil
    Gray, Jeffrey L.
    [J]. TETRAHEDRON LETTERS, 2006, 47 (22) : 3629 - 3631
  • [2] Inhibitors of protein tyrosine phosphatases: Next-generation drugs?
    Bialy, L
    Waldmann, H
    [J]. 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
    Brindle, NPJ
    Saharinen, P
    Alitalo, K
    [J]. CIRCULATION RESEARCH, 2006, 98 (08) : 1014 - 1023
  • [5] Tyrosine phosphatase inhibition augments collateral blood flow in a rat model of peripheral vascular disease
    Carr, AN
    Davis, MG
    Eby-Wilkens, E
    Howard, BW
    Towne, BA
    Dufresne, TE
    Peters, KG
    [J]. 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
    Chae, JK
    Kim, I
    Lim, ST
    Chung, MJ
    Kim, WH
    Kim, HG
    Ko, JK
    Koh, GY
    [J]. ARTERIOSCLEROSIS THROMBOSIS AND VASCULAR BIOLOGY, 2000, 20 (12) : 2573 - 2578
  • [7] Coordinated action of protein tyrosine phosphatases in insulin signal transduction
    Cheng, A
    Dubé, N
    Gu, F
    Tremblay, ML
    [J]. EUROPEAN JOURNAL OF BIOCHEMISTRY, 2002, 269 (04): : 1050 - 1059
  • [8] PTP-1B inhibitors:: Cyclopenta[d][1,2]-oxazine derivatives
    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
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (03) : 499 - 502
  • [9] Functional interaction of vascular endothelial-protein-tyrosine phosphatase with the Angiopoietin receptor Tie-2
    Fachinger, G
    Deutsch, U
    Risau, W
    [J]. ONCOGENE, 1999, 18 (43) : 5948 - 5953
  • [10] Growth factors acting via endothelial cell-specific receptor tyrosine kinases: VEGFs, angiopoietins, and ephrins in vascular development
    Gale, NW
    Yancopoulos, GD
    [J]. GENES & DEVELOPMENT, 1999, 13 (09) : 1055 - 1066