P-4 強力なTNF-α産生阻害活性を有する天然p-テルフェニル類の合成研究(ポスター発表の部)

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TNF-α is a potent multifunctional cytokine that mediates a variety of biological actions with a central role in the pathogenesis of many inflammatory diseases. Thus, inhibitors of TNF-α production in the activated mast cells and basophils are promising candidates for a new type of anti-allergic agent. In our search for bioactive compounds from edible Chinese mushrooms, we isolated a new potent antioxidant, vialinin A (1) along with atromentin, a mixture of ganbajunins D, and E from the dry fruiting bodies of Thelephora vialis. Recently, we found that 1 strongly inhibited TNF-α production in rat basophilic leukemia (RBL-2H3) cells: the IC_<50> was 90pM when the clinical immunosuppressant FK-506 was used in the same run as a positive standard (IC_<50>=0.25nM). In order to clarify the target molecule of 1 and develop a new anti-allergic drug, we have started synthetic studies on bioactive p-terphenyl derivatives. In this symposium, we present total synthesis of 1 and its related compounds. Vialinin A (1) was synthesized from sesamol in 11 steps with 28% overall yield. The key reactions include a double Suzuki coupling of electron-rich aryl triflate with phenylboronic acid, and an oxidative deprotection of bis-MOM ether. A similar strategy enabled us to prepare atromentin, ganbajunins D and E from bromanilic acid. Furthermore total synthesis of the proposed structure for ganbajunin C suggested the necessity for structural revision of this natural product.
天然有機化合物討論会の論文
2008-09-01

P-4 強力なTNF-α産生阻害活性を有する天然p-テルフェニル類の合成研究(ポスター発表の部)

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