Synthesis and nuclear factor-κB inhibitory activities of 6- or 7-methylchroman-2-carboxylic acid N-(substituted) phenylamides

Jae Hwan Kwak; Sun Woo Won; Tae Jeong Kim; Wonhui Yi; Eun Hwa Choi; Seung Chan Kim; Hyunjeong Park; Eunmiri Roh; Jae Kyung Jung; Bang Yeon Hwang; Jin Tae Hong; Youngsoo Kim; Jungsook Cho; Heesoon Lee

doi:10.1007/s12272-009-1131-3

Synthesis and nuclear factor-κB inhibitory activities of 6- or 7-methylchroman-2-carboxylic acid N-(substituted) phenylamides

Jae Hwan Kwak, Sun Woo Won, Tae Jeong Kim, Wonhui Yi, Eun Hwa Choi, Seung Chan Kim, Hyunjeong Park, Eunmiri Roh, Jae Kyung Jung, Bang Yeon Hwang, Jin Tae Hong, Youngsoo Kim, Jungsook Cho, Heesoon Lee

Hormel Institute

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

9 Scopus citations

Abstract

A series of 6- or 7-methylchroman-2-carboxylic acid N-(substituted) phenylamides (2a-s, 3a-s) were synthesized. Their abilities to inhibit nuclear factor-κB (NF-κB) activity were evaluated in lipopolysaccharide (LPS)-stimulated macrophage RAW 264.7 cells. Compounds with substituents such as -H, -CH₃, and -CF₃ on the phenyl ring were poor inhibitors of NF-κB. The most active NF-κB inhibitors contained 4-Cl (3s) and 4-OMe (3g) in the 7-methylchroman-2-carboxamide derivatives and 2-OH (2b) and 4-Cl (2s) in the 6-methylchroman-2-carboxamide derivatives (IC ₅₀: 20.2-24.0 μM). These were slightly more potent than a reference compound, KL-1156 (1) (IC₅₀: 43.9 μM).

Original language	English (US)
Pages (from-to)	167-175
Number of pages	9
Journal	Archives of Pharmacal Research
Volume	32
Issue number	2
DOIs	https://doi.org/10.1007/s12272-009-1131-3
State	Published - Feb 2009

Bibliographical note

Funding Information:
This work was supported by the research grant of the Chungbuk National University in 2007, the grant of the Korean Ministry of Education, Science and Technology (The Regional Core Research Program / Chungbuk BIT Research-Oriented University Consortium), and the Korea Science and Engineering Foundation (KOSEF) Grant funded by the Korea Government (MOST) (R13-2008-001-00000-00).

Keywords

6-Methylchroman-2-carboxamide
7-Methylchroman-2- carboxamide
NF-κB inhibitor

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Kwak, J. H., Won, S. W., Kim, T. J., Yi, W., Choi, E. H., Kim, S. C., Park, H., Roh, E., Jung, J. K., Hwang, B. Y., Hong, J. T., Kim, Y., Cho, J., & Lee, H. (2009). Synthesis and nuclear factor-κB inhibitory activities of 6- or 7-methylchroman-2-carboxylic acid N-(substituted) phenylamides. Archives of Pharmacal Research, 32(2), 167-175. https://doi.org/10.1007/s12272-009-1131-3

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abstract = "A series of 6- or 7-methylchroman-2-carboxylic acid N-(substituted) phenylamides (2a-s, 3a-s) were synthesized. Their abilities to inhibit nuclear factor-κB (NF-κB) activity were evaluated in lipopolysaccharide (LPS)-stimulated macrophage RAW 264.7 cells. Compounds with substituents such as -H, -CH3, and -CF3 on the phenyl ring were poor inhibitors of NF-κB. The most active NF-κB inhibitors contained 4-Cl (3s) and 4-OMe (3g) in the 7-methylchroman-2-carboxamide derivatives and 2-OH (2b) and 4-Cl (2s) in the 6-methylchroman-2-carboxamide derivatives (IC 50: 20.2-24.0 μM). These were slightly more potent than a reference compound, KL-1156 (1) (IC50: 43.9 μM).",

keywords = "6-Methylchroman-2-carboxamide, 7-Methylchroman-2- carboxamide, NF-κB inhibitor",

author = "Kwak, {Jae Hwan} and Won, {Sun Woo} and Kim, {Tae Jeong} and Wonhui Yi and Choi, {Eun Hwa} and Kim, {Seung Chan} and Hyunjeong Park and Eunmiri Roh and Jung, {Jae Kyung} and Hwang, {Bang Yeon} and Hong, {Jin Tae} and Youngsoo Kim and Jungsook Cho and Heesoon Lee",

note = "Funding Information: This work was supported by the research grant of the Chungbuk National University in 2007, the grant of the Korean Ministry of Education, Science and Technology (The Regional Core Research Program / Chungbuk BIT Research-Oriented University Consortium), and the Korea Science and Engineering Foundation (KOSEF) Grant funded by the Korea Government (MOST) (R13-2008-001-00000-00).",

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AU - Yi, Wonhui

AU - Choi, Eun Hwa

AU - Kim, Seung Chan

AU - Park, Hyunjeong

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AU - Jung, Jae Kyung

AU - Hwang, Bang Yeon

AU - Hong, Jin Tae

AU - Kim, Youngsoo

AU - Cho, Jungsook

AU - Lee, Heesoon

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N2 - A series of 6- or 7-methylchroman-2-carboxylic acid N-(substituted) phenylamides (2a-s, 3a-s) were synthesized. Their abilities to inhibit nuclear factor-κB (NF-κB) activity were evaluated in lipopolysaccharide (LPS)-stimulated macrophage RAW 264.7 cells. Compounds with substituents such as -H, -CH3, and -CF3 on the phenyl ring were poor inhibitors of NF-κB. The most active NF-κB inhibitors contained 4-Cl (3s) and 4-OMe (3g) in the 7-methylchroman-2-carboxamide derivatives and 2-OH (2b) and 4-Cl (2s) in the 6-methylchroman-2-carboxamide derivatives (IC 50: 20.2-24.0 μM). These were slightly more potent than a reference compound, KL-1156 (1) (IC50: 43.9 μM).

AB - A series of 6- or 7-methylchroman-2-carboxylic acid N-(substituted) phenylamides (2a-s, 3a-s) were synthesized. Their abilities to inhibit nuclear factor-κB (NF-κB) activity were evaluated in lipopolysaccharide (LPS)-stimulated macrophage RAW 264.7 cells. Compounds with substituents such as -H, -CH3, and -CF3 on the phenyl ring were poor inhibitors of NF-κB. The most active NF-κB inhibitors contained 4-Cl (3s) and 4-OMe (3g) in the 7-methylchroman-2-carboxamide derivatives and 2-OH (2b) and 4-Cl (2s) in the 6-methylchroman-2-carboxamide derivatives (IC 50: 20.2-24.0 μM). These were slightly more potent than a reference compound, KL-1156 (1) (IC50: 43.9 μM).

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Synthesis and nuclear factor-κB inhibitory activities of 6- or 7-methylchroman-2-carboxylic acid N-(substituted) phenylamides

Abstract

Bibliographical note

Keywords

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