Synthesis of three bromophenols from red algae as PTP1B inhibitors

摘要: Bromophenols are a set of natural products widely distributed in seaweed, most which exhibit interesting and useful biological activities. To develop reliable efficient synthetic route to these bromophenols, three them, 3,4-dibromo-5-(2′-bromo-3′,4′-dihydroxy-6′-methoxymethyl-benzyl)-benzene-1,2-diol (compound 9), 3,4-dibromo-5-(2′-bromo-6′-ethoxy methyl-3′,4′-dihydroxybenzyl)-benzene-1,2-diol 10), 3-bromo-4-(3′-bromo-4′,5′-dihydroxy benzyl)-5-(ethoxymethyl)-benzene-1,2-diol 14), isolated from red marine algae, have been synthesized eight steps with an overall yield 14.4%, 18.2% respectively, via practical approach employing bromination, Wolff-Kishner-Huang reduction Friedel-Crafts reaction as key steps. The protein tyrosine phosphatase 1B (PTP1B) inhibitory activities the compounds were evaluated by colorimetric assay. results show that moderate PTP1B inhibitors. synthesis bromophenol derivatives makes vivo studies their structure-activity relationships inhibition activity against possible.