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    Please use this identifier to cite or link to this item: http://asiair.asia.edu.tw/ir/handle/310904400/17237

    Title: Regioselective Synthesis of 3-(1H-indol-3-yl)-5-(1H-indole-3-carbonyl)-4-hydroxyfuroic Acids: A Route to Hydroxyfuroic Acid Based Insulin Receptor Activators
    Authors: Chou, Shan-Yen;蔡建鈞;Tsai, Henry Jan-Jen
    Contributors: 保健營養生技學系
    Keywords: insulin receptor activator;regioselective synthesis;hydroxyfuroic acid
    Date: 2010-09
    Issue Date: 2012-11-26 10:30:23 (UTC+8)
    Abstract: A new class of insulin receptor activator with a hydroxyfuroic acid in place of a hydroxyquinone moiety is reported. The synthesis of 3-(1H-indol-3-yl)-5-(1H-indole-3-carbonyl)-4-hydroxyfuroic acids (26–30) requires seven major steps. Key elements in the syntheses include (1) sequential preparation of two 4-(N-protected indole)-3-methoxy-furoic 2,5-dicarboxylic esters (4 and 6); (2) regioselective conversion of the furoic diacid 8 into its C-5 methyl ester 10 with methyl chloroformate; and (3) acylation of 10 by a 7-substituted indole under a mild condition. This study demonstrates a feasible route of synthesizing insulin receptor activators with a hydroxyfuroic acid scaffold. Among those hydroxyfuroic acid compounds, compound 28 demonstrates insulin receptor activation potential comparable to Merck's compound 2 with a dihydroxybenzoquinone scaffold. Drug Dev Res 72: 247–258, 2011. © 2010 Wiley-Liss, Inc.
    Relation: DRUG DEVELOPMENT RESEARCH, 72(3):247-258.
    Appears in Collections:[食品營養與保健生技學系] 期刊論文

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