Synthesis of chroman-2-carboxylic acid N-(substituted)phenylamides and their inhibitory effect on nuclear factor-κB (NF-κB) activation

Jae Hwan Kwak; Sun Woo Won; Tae Jeong Kim; Eunmiri Roh; Han Young Kang; Hyo Won Lee; Jae Kyung Jung; Bang Yeon Hwang; Youngsoo Kim; Jungsook Cho; Heesoon Lee

doi:10.1007/s12272-001-1131-4

Synthesis of chroman-2-carboxylic acid N-(substituted)phenylamides and their inhibitory effect on nuclear factor-κB (NF-κB) activation

Jae Hwan Kwak, Sun Woo Won, Tae Jeong Kim, Eunmiri Roh, Han Young Kang, Hyo Won Lee, Jae Kyung Jung, Bang Yeon Hwang, Youngsoo Kim, Jungsook Cho, Heesoon Lee

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Abstract

A series of chroman-2-carboxylic acid N-(substituted)phenylamides (2a-s, 3a-j) were synthesized. Their ability to inhibit nuclear factor-κB (NF-κB) activity was evaluated in lipopolysaccharide (LPS)-stimulated macrophage RAW 264.7 cells and their antioxidant activity was examined. NF-κB inhibition by chroman compounds was not related to their antioxidant activity. Compounds with -H, -NO₂ monosubstituents and -OCH ₃, -CF₃ disubstituents on the phenyl ring were poor inhibitors of NF-kB activity. Compounds with -CH₃, -CF₃, -Cl monosubstituents or -Cl, -CH₃ disubstituents exhibited moderate to good NF-κB activity inhibition (IC₅₀: 18.2-95.8 μM). The most active NF-κB inhibitor, 2s, contained a 4-Cl (IC₅₀: 18.2 μM) substituent on the phenyl ring and was slightly more potent than the compound KL-1156 (1) (IC₅₀: 43.9 μM).

Original language	English (US)
Pages (from-to)	133-141
Number of pages	9
Journal	Archives of Pharmacal Research
Volume	31
Issue number	2
DOIs	https://doi.org/10.1007/s12272-001-1131-4
State	Published - Feb 2008
Externally published	Yes

Bibliographical note

Funding Information:
This work was supported by the Korea Research Foundation Grant funded by the Korean Government (MOEHRD) (The Regional Research Universities Program/Chungbuk BIT Research-Oriented University Consortium).

Keywords

Chroman-2-carboxamide
NF-κB inhibitor

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title = "Synthesis of chroman-2-carboxylic acid N-(substituted)phenylamides and their inhibitory effect on nuclear factor-κB (NF-κB) activation",

abstract = "A series of chroman-2-carboxylic acid N-(substituted)phenylamides (2a-s, 3a-j) were synthesized. Their ability to inhibit nuclear factor-κB (NF-κB) activity was evaluated in lipopolysaccharide (LPS)-stimulated macrophage RAW 264.7 cells and their antioxidant activity was examined. NF-κB inhibition by chroman compounds was not related to their antioxidant activity. Compounds with -H, -NO2 monosubstituents and -OCH 3, -CF3 disubstituents on the phenyl ring were poor inhibitors of NF-kB activity. Compounds with -CH3, -CF3, -Cl monosubstituents or -Cl, -CH3 disubstituents exhibited moderate to good NF-κB activity inhibition (IC50: 18.2-95.8 μM). The most active NF-κB inhibitor, 2s, contained a 4-Cl (IC50: 18.2 μM) substituent on the phenyl ring and was slightly more potent than the compound KL-1156 (1) (IC50: 43.9 μM).",

keywords = "Chroman-2-carboxamide, NF-κB inhibitor",

author = "Kwak, {Jae Hwan} and Won, {Sun Woo} and Kim, {Tae Jeong} and Eunmiri Roh and Kang, {Han Young} and Lee, {Hyo Won} and Jung, {Jae Kyung} and Hwang, {Bang Yeon} and Youngsoo Kim and Jungsook Cho and Heesoon Lee",

note = "Funding Information: This work was supported by the Korea Research Foundation Grant funded by the Korean Government (MOEHRD) (The Regional Research Universities Program/Chungbuk BIT Research-Oriented University Consortium).",

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doi = "10.1007/s12272-001-1131-4",

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pages = "133--141",

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AU - Kwak, Jae Hwan

AU - Won, Sun Woo

AU - Kim, Tae Jeong

AU - Roh, Eunmiri

AU - Kang, Han Young

AU - Lee, Hyo Won

AU - Jung, Jae Kyung

AU - Hwang, Bang Yeon

AU - Kim, Youngsoo

AU - Cho, Jungsook

AU - Lee, Heesoon

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PY - 2008/2

Y1 - 2008/2

N2 - A series of chroman-2-carboxylic acid N-(substituted)phenylamides (2a-s, 3a-j) were synthesized. Their ability to inhibit nuclear factor-κB (NF-κB) activity was evaluated in lipopolysaccharide (LPS)-stimulated macrophage RAW 264.7 cells and their antioxidant activity was examined. NF-κB inhibition by chroman compounds was not related to their antioxidant activity. Compounds with -H, -NO2 monosubstituents and -OCH 3, -CF3 disubstituents on the phenyl ring were poor inhibitors of NF-kB activity. Compounds with -CH3, -CF3, -Cl monosubstituents or -Cl, -CH3 disubstituents exhibited moderate to good NF-κB activity inhibition (IC50: 18.2-95.8 μM). The most active NF-κB inhibitor, 2s, contained a 4-Cl (IC50: 18.2 μM) substituent on the phenyl ring and was slightly more potent than the compound KL-1156 (1) (IC50: 43.9 μM).

AB - A series of chroman-2-carboxylic acid N-(substituted)phenylamides (2a-s, 3a-j) were synthesized. Their ability to inhibit nuclear factor-κB (NF-κB) activity was evaluated in lipopolysaccharide (LPS)-stimulated macrophage RAW 264.7 cells and their antioxidant activity was examined. NF-κB inhibition by chroman compounds was not related to their antioxidant activity. Compounds with -H, -NO2 monosubstituents and -OCH 3, -CF3 disubstituents on the phenyl ring were poor inhibitors of NF-kB activity. Compounds with -CH3, -CF3, -Cl monosubstituents or -Cl, -CH3 disubstituents exhibited moderate to good NF-κB activity inhibition (IC50: 18.2-95.8 μM). The most active NF-κB inhibitor, 2s, contained a 4-Cl (IC50: 18.2 μM) substituent on the phenyl ring and was slightly more potent than the compound KL-1156 (1) (IC50: 43.9 μM).

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KW - NF-κB inhibitor

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Synthesis of chroman-2-carboxylic acid N-(substituted)phenylamides and their inhibitory effect on nuclear factor-κB (NF-κB) activation

Abstract

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