2-Aryl-3,3,3-trifluoro-2-hydroxypropionic acids: A new class of protein tyrosine phosphatase 1B inhibitors

David R. Adams; Achamma Abraham; Jun Asano; Catherine Breslin; C. A J Dick; Ulrich Ixkes; Blair F. Johnston; Derek Johnston; Justin Kewnay; Simon P. Mackay; Simon J. MacKenzie; Morag McFarlane; Lee Mitchell; Daniel Spinks; Yasuo Takano

doi:10.1016/j.bmcl.2007.09.069

2-Aryl-3,3,3-trifluoro-2-hydroxypropionic acids: A new class of protein tyrosine phosphatase 1B inhibitors

David R. Adams, Achamma Abraham, Jun Asano, Catherine Breslin, C. A J Dick, Ulrich Ixkes, Blair F. Johnston, Derek Johnston, Justin Kewnay, Simon P. Mackay, Simon J. MacKenzie, Morag McFarlane, Lee Mitchell, Daniel Spinks, Yasuo Takano

School of Engineering & Physical Sciences

Research output: Contribution to journal › Article › peer-review

29 Citations (Scopus)

Abstract

A new series of non-peptidic, mono-acid protein tyrosine phosphatase 1B (PTP1B) inhibitors has been identified by structure-based design. Compounds with 2-(indol-3-yl)- and 2-phenyl-3,3,3-trifluoro-2-hydroxypropionic acid core units targeted at the enzyme's primary site and a hydrophobic chlorophenylthiazole extension in its 2° site exhibit 3-60 µM IC₅₀s for PTP1B inhibition in an Sf9 cell-based assay. © 2007 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	6579-6583
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	17
Issue number	23
DOIs	https://doi.org/10.1016/j.bmcl.2007.09.069
Publication status	Published - 1 Dec 2007

Keywords

Diabetes
Indole
Inhibitor
Insulin resistance
Insulin sensitivity
Obesity
Phospho-tyrosine
Protein tyrosine phosphatase 1B
PTP1B
Structure-based design
Thiazole

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.bmcl.2007.09.069

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Adams, D. R., Abraham, A., Asano, J., Breslin, C., Dick, C. A. J., Ixkes, U., Johnston, B. F., Johnston, D., Kewnay, J., Mackay, S. P., MacKenzie, S. J., McFarlane, M., Mitchell, L., Spinks, D., & Takano, Y. (2007). 2-Aryl-3,3,3-trifluoro-2-hydroxypropionic acids: A new class of protein tyrosine phosphatase 1B inhibitors. Bioorganic and Medicinal Chemistry Letters, 17(23), 6579-6583. https://doi.org/10.1016/j.bmcl.2007.09.069

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abstract = "A new series of non-peptidic, mono-acid protein tyrosine phosphatase 1B (PTP1B) inhibitors has been identified by structure-based design. Compounds with 2-(indol-3-yl)- and 2-phenyl-3,3,3-trifluoro-2-hydroxypropionic acid core units targeted at the enzyme's primary site and a hydrophobic chlorophenylthiazole extension in its 2° site exhibit 3-60 µM IC50s for PTP1B inhibition in an Sf9 cell-based assay. {\textcopyright} 2007 Elsevier Ltd. All rights reserved.",

keywords = "Diabetes, Indole, Inhibitor, Insulin resistance, Insulin sensitivity, Obesity, Phospho-tyrosine, Protein tyrosine phosphatase 1B, PTP1B, Structure-based design, Thiazole",

author = "Adams, {David R.} and Achamma Abraham and Jun Asano and Catherine Breslin and Dick, {C. A J} and Ulrich Ixkes and Johnston, {Blair F.} and Derek Johnston and Justin Kewnay and Mackay, {Simon P.} and MacKenzie, {Simon J.} and Morag McFarlane and Lee Mitchell and Daniel Spinks and Yasuo Takano",

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Adams, DR, Abraham, A, Asano, J, Breslin, C, Dick, CAJ, Ixkes, U, Johnston, BF, Johnston, D, Kewnay, J, Mackay, SP, MacKenzie, SJ, McFarlane, M, Mitchell, L, Spinks, D & Takano, Y 2007, '2-Aryl-3,3,3-trifluoro-2-hydroxypropionic acids: A new class of protein tyrosine phosphatase 1B inhibitors', Bioorganic and Medicinal Chemistry Letters, vol. 17, no. 23, pp. 6579-6583. https://doi.org/10.1016/j.bmcl.2007.09.069

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T2 - A new class of protein tyrosine phosphatase 1B inhibitors

AU - Adams, David R.

AU - Abraham, Achamma

AU - Asano, Jun

AU - Breslin, Catherine

AU - Dick, C. A J

AU - Ixkes, Ulrich

AU - Johnston, Blair F.

AU - Johnston, Derek

AU - Kewnay, Justin

AU - Mackay, Simon P.

AU - MacKenzie, Simon J.

AU - McFarlane, Morag

AU - Mitchell, Lee

AU - Spinks, Daniel

AU - Takano, Yasuo

PY - 2007/12/1

Y1 - 2007/12/1

N2 - A new series of non-peptidic, mono-acid protein tyrosine phosphatase 1B (PTP1B) inhibitors has been identified by structure-based design. Compounds with 2-(indol-3-yl)- and 2-phenyl-3,3,3-trifluoro-2-hydroxypropionic acid core units targeted at the enzyme's primary site and a hydrophobic chlorophenylthiazole extension in its 2° site exhibit 3-60 µM IC50s for PTP1B inhibition in an Sf9 cell-based assay. © 2007 Elsevier Ltd. All rights reserved.

AB - A new series of non-peptidic, mono-acid protein tyrosine phosphatase 1B (PTP1B) inhibitors has been identified by structure-based design. Compounds with 2-(indol-3-yl)- and 2-phenyl-3,3,3-trifluoro-2-hydroxypropionic acid core units targeted at the enzyme's primary site and a hydrophobic chlorophenylthiazole extension in its 2° site exhibit 3-60 µM IC50s for PTP1B inhibition in an Sf9 cell-based assay. © 2007 Elsevier Ltd. All rights reserved.

KW - Diabetes

KW - Indole

KW - Inhibitor

KW - Insulin resistance

KW - Insulin sensitivity

KW - Obesity

KW - Phospho-tyrosine

KW - Protein tyrosine phosphatase 1B

KW - PTP1B

KW - Structure-based design

KW - Thiazole

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DO - 10.1016/j.bmcl.2007.09.069

M3 - Article

SN - 0960-894X

VL - 17

SP - 6579

EP - 6583

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 23

ER -

2-Aryl-3,3,3-trifluoro-2-hydroxypropionic acids: A new class of protein tyrosine phosphatase 1B inhibitors

Abstract

Keywords

UN SDGs

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