Furanyl-1,3-thiazol-2-yl and benzoxazol-5-yl acetic acid derivatives: Novel classes of heparanase inhibitor

Eddie Mckenzie; Stephen M. Courtney; Philip A. Hay; Richard T. Buck; Claire S. Colville; David J. Phillips; David I C Scopes; Faye C. Pollard; Martin J. Page; James M. Bennett; Margaret L. Hircock; Edward A. McKenzie; Maina Bhaman; Robert Felix; Colin R. Stubberfield; Paul R. Turner

doi:10.1016/j.bmcl.2005.03.014

Furanyl-1,3-thiazol-2-yl and benzoxazol-5-yl acetic acid derivatives: Novel classes of heparanase inhibitor

Eddie Mckenzie, Stephen M. Courtney, Philip A. Hay, Richard T. Buck, Claire S. Colville, David J. Phillips, David I C Scopes, Faye C. Pollard, Martin J. Page, James M. Bennett, Margaret L. Hircock, Edward A. McKenzie, Maina Bhaman, Robert Felix, Colin R. Stubberfield, Paul R. Turner

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Abstract

Using a furanylthiazole acetic acid as a starting point, a novel series of benzoxazol-5-yl acetic acid derivatives have been identified as heparanase inhibitors. Several compounds possess an IC50 of ∼200 nM against heparanase, for example, trans 2-[4-[3-(3,4-dichlorophenylamino)-3-oxo-1- propenyl]-2-fluorophenyl]benzoxazol-5-yl acetic acid (16e). Several of the compounds show anti-angiogenic properties. Improvement to the DMPK profile of compounds has provided compounds of potential use in in vivo models. © 2005 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	2295-2299
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	15
Issue number	9
DOIs	https://doi.org/10.1016/j.bmcl.2005.03.014
Publication status	Published - 2 May 2005

Keywords

β-glucuronidase
Angiogenesis
Benzoxazole
Heparanase
Metastasis

Research Beacons, Institutes and Platforms

Manchester Institute of Biotechnology

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10.1016/j.bmcl.2005.03.014

Cite this

Mckenzie, E., Courtney, S. M., Hay, P. A., Buck, R. T., Colville, C. S., Phillips, D. J., Scopes, D. I. C., Pollard, F. C., Page, M. J., Bennett, J. M., Hircock, M. L., McKenzie, E. A., Bhaman, M., Felix, R., Stubberfield, C. R., & Turner, P. R. (2005). Furanyl-1,3-thiazol-2-yl and benzoxazol-5-yl acetic acid derivatives: Novel classes of heparanase inhibitor. Bioorganic and Medicinal Chemistry Letters, 15(9), 2295-2299. https://doi.org/10.1016/j.bmcl.2005.03.014

@article{b39b31d9149f469793466446924cc1ec,

title = "Furanyl-1,3-thiazol-2-yl and benzoxazol-5-yl acetic acid derivatives: Novel classes of heparanase inhibitor",

abstract = "Using a furanylthiazole acetic acid as a starting point, a novel series of benzoxazol-5-yl acetic acid derivatives have been identified as heparanase inhibitors. Several compounds possess an IC50 of ∼200 nM against heparanase, for example, trans 2-[4-[3-(3,4-dichlorophenylamino)-3-oxo-1- propenyl]-2-fluorophenyl]benzoxazol-5-yl acetic acid (16e). Several of the compounds show anti-angiogenic properties. Improvement to the DMPK profile of compounds has provided compounds of potential use in in vivo models. {\textcopyright} 2005 Elsevier Ltd. All rights reserved.",

keywords = "β-glucuronidase, Angiogenesis, Benzoxazole, Heparanase, Metastasis",

author = "Eddie Mckenzie and Courtney, {Stephen M.} and Hay, {Philip A.} and Buck, {Richard T.} and Colville, {Claire S.} and Phillips, {David J.} and Scopes, {David I C} and Pollard, {Faye C.} and Page, {Martin J.} and Bennett, {James M.} and Hircock, {Margaret L.} and McKenzie, {Edward A.} and Maina Bhaman and Robert Felix and Stubberfield, {Colin R.} and Turner, {Paul R.}",

year = "2005",

month = may,

day = "2",

doi = "10.1016/j.bmcl.2005.03.014",

language = "English",

volume = "15",

pages = "2295--2299",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "1464-3405",

publisher = "Elsevier BV",

number = "9",

}

Mckenzie, E, Courtney, SM, Hay, PA, Buck, RT, Colville, CS, Phillips, DJ, Scopes, DIC, Pollard, FC, Page, MJ, Bennett, JM, Hircock, ML, McKenzie, EA, Bhaman, M, Felix, R, Stubberfield, CR & Turner, PR 2005, 'Furanyl-1,3-thiazol-2-yl and benzoxazol-5-yl acetic acid derivatives: Novel classes of heparanase inhibitor', Bioorganic and Medicinal Chemistry Letters, vol. 15, no. 9, pp. 2295-2299. https://doi.org/10.1016/j.bmcl.2005.03.014

TY - JOUR

T1 - Furanyl-1,3-thiazol-2-yl and benzoxazol-5-yl acetic acid derivatives: Novel classes of heparanase inhibitor

AU - Mckenzie, Eddie

AU - Courtney, Stephen M.

AU - Hay, Philip A.

AU - Buck, Richard T.

AU - Colville, Claire S.

AU - Phillips, David J.

AU - Scopes, David I C

AU - Pollard, Faye C.

AU - Page, Martin J.

AU - Bennett, James M.

AU - Hircock, Margaret L.

AU - McKenzie, Edward A.

AU - Bhaman, Maina

AU - Felix, Robert

AU - Stubberfield, Colin R.

AU - Turner, Paul R.

PY - 2005/5/2

Y1 - 2005/5/2

N2 - Using a furanylthiazole acetic acid as a starting point, a novel series of benzoxazol-5-yl acetic acid derivatives have been identified as heparanase inhibitors. Several compounds possess an IC50 of ∼200 nM against heparanase, for example, trans 2-[4-[3-(3,4-dichlorophenylamino)-3-oxo-1- propenyl]-2-fluorophenyl]benzoxazol-5-yl acetic acid (16e). Several of the compounds show anti-angiogenic properties. Improvement to the DMPK profile of compounds has provided compounds of potential use in in vivo models. © 2005 Elsevier Ltd. All rights reserved.

AB - Using a furanylthiazole acetic acid as a starting point, a novel series of benzoxazol-5-yl acetic acid derivatives have been identified as heparanase inhibitors. Several compounds possess an IC50 of ∼200 nM against heparanase, for example, trans 2-[4-[3-(3,4-dichlorophenylamino)-3-oxo-1- propenyl]-2-fluorophenyl]benzoxazol-5-yl acetic acid (16e). Several of the compounds show anti-angiogenic properties. Improvement to the DMPK profile of compounds has provided compounds of potential use in in vivo models. © 2005 Elsevier Ltd. All rights reserved.

KW - β-glucuronidase

KW - Angiogenesis

KW - Benzoxazole

KW - Heparanase

KW - Metastasis

U2 - 10.1016/j.bmcl.2005.03.014

DO - 10.1016/j.bmcl.2005.03.014

M3 - Article

SN - 1464-3405

VL - 15

SP - 2295

EP - 2299

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 9

ER -

Furanyl-1,3-thiazol-2-yl and benzoxazol-5-yl acetic acid derivatives: Novel classes of heparanase inhibitor

Abstract

Keywords

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