title: Synthesis and nuclear factor-kappaB inhibitory activities of 6- or 7-methylchroman-2-carboxylic acid N-(substituted) phenylamides.
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-kappaB (NF-kappaB) activity were evaluated in lipopolysaccharide (LPS)-stimulated macrophage RAW 264.7 cells. Compounds with substituents such as -H, -CH(3), and -CF(3) on the phenyl ring were poor inhibitors of NF-kappaB. The most active NF-kappaB 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 microM). These were slightly more potent than a reference compound, KL-1156 (1) (IC(50): 43.9 microM).
authors.affiliation: College of Pharmacy, Chungbuk National University, Cheongju 361-763, Korea.
authors.forename: Jae-Hwan
authors.initials: JH
authors.lastname: Kwak
authors.forename: Sun-Woo
authors.initials: SW
authors.lastname: Won
authors.forename: Tae-Jeong
authors.initials: TJ
authors.lastname: Kim
authors.forename: Wonhui
authors.initials: W
authors.lastname: Yi
authors.forename: Eun-Hwa
authors.initials: EH
authors.lastname: Choi
authors.forename: Seung-Chan
authors.initials: SC
authors.lastname: Kim
authors.forename: Hyunjeong
authors.initials: H
authors.lastname: Park
authors.forename: Eunmiri
authors.initials: E
authors.lastname: Roh
authors.forename: Jae-Kyung
authors.initials: JK
authors.lastname: Jung
authors.forename: Bang Yeon
authors.initials: BY
authors.lastname: Hwang
authors.forename: Jin Tae
authors.initials: JT
authors.lastname: Hong
authors.forename: Youngsoo
authors.initials: Y
authors.lastname: Kim
authors.forename: Jungsook
authors.initials: J
authors.lastname: Cho
authors.forename: Heesoon
authors.initials: H
authors.lastname: Lee
mesh_terms: D000818:Animals; D002460:Cell Line; D002839:Chromans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D020128:Inhibitory Concentration 50; D008070:Lipopolysaccharides / Q000494:pharmacology; D008264:Macrophages / Q000187:drug effects / Q000378:metabolism; D051379:Mice; D015394:Molecular Structure; D016328:NF-kappa B / Q000037:antagonists & inhibitors*; D013329:Structure-Activity Relationship
chemical_list: C495393:6-hydroxy-7-methoxychroman-2-carboxylic acid phenylamide; D002839:Chromans; D008070:Lipopolysaccharides; D016328:NF-kappa B