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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12 Scopus citations

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 languageEnglish (US)
Pages (from-to)133-141
Number of pages9
JournalArchives of Pharmacal Research
Volume31
Issue number2
DOIs
StatePublished - Feb 2008
Externally publishedYes

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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