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

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8 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 languageEnglish (US)
Pages (from-to)167-175
Number of pages9
JournalArchives of Pharmacal Research
Volume32
Issue number2
DOIs
StatePublished - Feb 1 2009

Keywords

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

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