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

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 a...

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Veröffentlicht in:Bioorganic & medicinal chemistry letters 2012-04, Vol.22 (7), p.2385-2387
Hauptverfasser: Ye, Yue Qi, Onose, Jun-ichi, Abe, Naoki, Koshino, Hiroyuki, Takahashi, Shunya
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Sprache:eng
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Zusammenfassung: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 (IC50=0.02nM) 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.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2012.02.034