title: Design and synthesis of a vialinin A analog with a potent inhibitory activity of TNF-α production and its transformation into a couple of bioprobes.
abstract: Vialinin A (1) is an extremely potent inhibitor against tumor necrosis factor (TNF)-α production in rat basophilic leukemia (RBL-2H3) cells. This Letter describes the design and synthesis of its advanced analog, 5',6'-dimethyl-1,1':4'1″-terphenyl-2',3',4,4″-tetraol (2) with a comparable inhibitory activity (IC(50)=0.02 nM) to that of 1. The synthesis involved double Suzuki-Miyaura coupling as a key step, and required only five steps from commercially available 3,4-dimethylphenol. For identification of the target molecule, fluorescent and biotinylated derivatives of 2 were prepared through a 'click' coupling process.
authors.affiliation: RIKEN ASI, Wako-shi, Saitama 351-0198, Japan.
authors.forename: Yue Qi
authors.initials: YQ
authors.lastname: Ye
authors.forename: Jun-ichi
authors.initials: J
authors.lastname: Onose
authors.forename: Naoki
authors.initials: N
authors.lastname: Abe
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Koshino
authors.forename: Shunya
authors.initials: S
authors.lastname: Takahashi
mesh_terms: D000818:Animals; D019921:Biotinylation; D045744:Cell Line, Tumor; D015195:Drug Design; D005453:Fluorescence; D007938:Leukemia / Q000378:metabolism / Q000473:pathology; D015335:Molecular Probes / Q000138:chemical synthesis*; D015394:Molecular Structure; D051381:Rats; D013730:Terphenyl Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D014409:Tumor Necrosis Factor-alpha / Q000037:antagonists & inhibitors* / Q000096:biosynthesis; D014992:Xylenes / Q000737:chemistry*
chemical_list: D015335:Molecular Probes; D013730:Terphenyl Compounds; D014409:Tumor Necrosis Factor-alpha; D014992:Xylenes; C508745:vialinin A; C063628:3,4-dimethylphenol