Synthesis and biological evaluation of benzenesulfonamide-substituted 4-(6-alkylpyridin-2-yl)-5-(quinoxalin-6-yl)imidazoles as transforming growth factor-β type 1 receptor kinase inhibitors

Dae Kee Kim; Sun Hee Jung; Ho Soon Lee; Purushottam M. Dewang

doi:10.1016/j.ejmech.2008.03.024

Synthesis and biological evaluation of benzenesulfonamide-substituted 4-(6-alkylpyridin-2-yl)-5-(quinoxalin-6-yl)imidazoles as transforming growth factor-β type 1 receptor kinase inhibitors

Dae Kee Kim, Sun Hee Jung, Ho Soon Lee, Purushottam M. Dewang

Department of Pharmaceutical Sciences

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

23 Scopus citations

Abstract

A series of benzenesulfonamide-substituted 4-(6-alkylpyridin-2-yl)-5-(quinoxalin-6-yl)imidazoles (15a-l) have been synthesized and evaluated for their ALK5 inhibitory activity in cell-based luciferase reporter assays. Among them, 4-[5-(6-methylpyridin-2-yl)-4-(quinoxalin-6-yl)-1H-imidazol-2-ylmethyl]b enzenesulfonamide (15b) and 4-[5-(6-ethylpyridin-2-yl)-4-(quinoxalin-6-yl)-1H-imidazol-2-ylmethyl]be nzenesulfonamide (15c) showed more than 90% inhibition at 0.5 μM in a luciferase reporter assay using HaCaT cells transiently transfected with p3TP-luc reporter construct, but inhibited p38α MAP kinase activity only 11 and 8% at a concentration of 10 μM, respectively.

Original language	English
Pages (from-to)	568-576
Number of pages	9
Journal	European Journal of Medicinal Chemistry
Volume	44
Issue number	2
DOIs	https://doi.org/10.1016/j.ejmech.2008.03.024
State	Published - Feb 2009

Bibliographical note

Funding Information:
This work was supported in part by the grants from Ministry of Commerce, Industry and Energy, Korea (M1-0310-43-0001 and M1-0310-43-0002).

Keywords

ALK5 inhibitors
Cancer
Fibrosis
Transforming growth factor-β (TGF-β)

UN SDGs

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

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10.1016/j.ejmech.2008.03.024

Cite this

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title = "Synthesis and biological evaluation of benzenesulfonamide-substituted 4-(6-alkylpyridin-2-yl)-5-(quinoxalin-6-yl)imidazoles as transforming growth factor-β type 1 receptor kinase inhibitors",

abstract = "A series of benzenesulfonamide-substituted 4-(6-alkylpyridin-2-yl)-5-(quinoxalin-6-yl)imidazoles (15a-l) have been synthesized and evaluated for their ALK5 inhibitory activity in cell-based luciferase reporter assays. Among them, 4-[5-(6-methylpyridin-2-yl)-4-(quinoxalin-6-yl)-1H-imidazol-2-ylmethyl]b enzenesulfonamide (15b) and 4-[5-(6-ethylpyridin-2-yl)-4-(quinoxalin-6-yl)-1H-imidazol-2-ylmethyl]be nzenesulfonamide (15c) showed more than 90% inhibition at 0.5 μM in a luciferase reporter assay using HaCaT cells transiently transfected with p3TP-luc reporter construct, but inhibited p38α MAP kinase activity only 11 and 8% at a concentration of 10 μM, respectively.",

keywords = "ALK5 inhibitors, Cancer, Fibrosis, Transforming growth factor-β (TGF-β)",

author = "Kim, {Dae Kee} and Jung, {Sun Hee} and Lee, {Ho Soon} and Dewang, {Purushottam M.}",

note = "Funding Information: This work was supported in part by the grants from Ministry of Commerce, Industry and Energy, Korea (M1-0310-43-0001 and M1-0310-43-0002). ",

year = "2009",

month = feb,

doi = "10.1016/j.ejmech.2008.03.024",

language = "English",

volume = "44",

pages = "568--576",

journal = "European Journal of Medicinal Chemistry",

issn = "0223-5234",

publisher = "Elsevier Masson s.r.l.",

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}

Synthesis and biological evaluation of benzenesulfonamide-substituted 4-(6-alkylpyridin-2-yl)-5-(quinoxalin-6-yl)imidazoles as transforming growth factor-β type 1 receptor kinase inhibitors. / Kim, Dae Kee; Jung, Sun Hee; Lee, Ho Soon et al.
In: European Journal of Medicinal Chemistry, Vol. 44, No. 2, 02.2009, p. 568-576.

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

TY - JOUR

T1 - Synthesis and biological evaluation of benzenesulfonamide-substituted 4-(6-alkylpyridin-2-yl)-5-(quinoxalin-6-yl)imidazoles as transforming growth factor-β type 1 receptor kinase inhibitors

AU - Kim, Dae Kee

AU - Jung, Sun Hee

AU - Lee, Ho Soon

AU - Dewang, Purushottam M.

N1 - Funding Information: This work was supported in part by the grants from Ministry of Commerce, Industry and Energy, Korea (M1-0310-43-0001 and M1-0310-43-0002).

PY - 2009/2

Y1 - 2009/2

N2 - A series of benzenesulfonamide-substituted 4-(6-alkylpyridin-2-yl)-5-(quinoxalin-6-yl)imidazoles (15a-l) have been synthesized and evaluated for their ALK5 inhibitory activity in cell-based luciferase reporter assays. Among them, 4-[5-(6-methylpyridin-2-yl)-4-(quinoxalin-6-yl)-1H-imidazol-2-ylmethyl]b enzenesulfonamide (15b) and 4-[5-(6-ethylpyridin-2-yl)-4-(quinoxalin-6-yl)-1H-imidazol-2-ylmethyl]be nzenesulfonamide (15c) showed more than 90% inhibition at 0.5 μM in a luciferase reporter assay using HaCaT cells transiently transfected with p3TP-luc reporter construct, but inhibited p38α MAP kinase activity only 11 and 8% at a concentration of 10 μM, respectively.

AB - A series of benzenesulfonamide-substituted 4-(6-alkylpyridin-2-yl)-5-(quinoxalin-6-yl)imidazoles (15a-l) have been synthesized and evaluated for their ALK5 inhibitory activity in cell-based luciferase reporter assays. Among them, 4-[5-(6-methylpyridin-2-yl)-4-(quinoxalin-6-yl)-1H-imidazol-2-ylmethyl]b enzenesulfonamide (15b) and 4-[5-(6-ethylpyridin-2-yl)-4-(quinoxalin-6-yl)-1H-imidazol-2-ylmethyl]be nzenesulfonamide (15c) showed more than 90% inhibition at 0.5 μM in a luciferase reporter assay using HaCaT cells transiently transfected with p3TP-luc reporter construct, but inhibited p38α MAP kinase activity only 11 and 8% at a concentration of 10 μM, respectively.

KW - ALK5 inhibitors

KW - Cancer

KW - Fibrosis

KW - Transforming growth factor-β (TGF-β)

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Synthesis and biological evaluation of benzenesulfonamide-substituted 4-(6-alkylpyridin-2-yl)-5-(quinoxalin-6-yl)imidazoles as transforming growth factor-β type 1 receptor kinase inhibitors

Abstract

Bibliographical note

Keywords

UN SDGs

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