Synthesis and protein tyrosine phosphatase 1B inhibition activities of two new synthetic bromophenols and their methoxy derivatives |
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| Authors: | Yongchao Cui Dayong Shi Zhiqiang Hu |
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| Institution: | (1) Department of Chemistry, Selcuk University, 42031 Konya, Turkey; |
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| Abstract: | 3-bromo-4,5-bis(2,3-dibromo-4,5-dihydroxybenzyl)-1,2-benzenediol (1) is a natural bromophenol isolated from the red algae Rhodomela confervoides that exhibits significant inhibition against protein tyrosine phosphatase 1B (PTP1B). Based on its activity, we synthesized
two new synthetic bromophenols and their methoxy derivatives from vanillin using the structure of natural bromophenol 1 as a scaffold. The structures of these bromophenols were elucidated from 1H NMR, 13C NMR, and high resolution electron ionization mass spectrometry as 2,3-dibromo-1-(2′-bromo-6′-(3″,4″-dimethoxybenzyl)-3′,4′-dimethoxybenzyl)-4,5-dimethoxybenzene
(2), 2,3-dibromo-1-(2′-bromo-6′-(2″-bromo-4″,5″-dimethoxybenzyl)-3′,4′-dimethoxybenzyl)-4,5-dimethoxybenzene (3), 3,4-dibromo-5-(2′-bromo-6′-(2″-bromo-4″,5″-dihydroxybenzyl)-3′,4′-dihydroxybenzyl)pyrocatechol (4) and 3,4-dibromo-5-(2′-bromo-6′-(3″,4″-dihydroxybenzyl)-3′,4′-dihydroxybenzyl)pyrocatechol (5). PTP1B inhibition activities of these compounds were evaluated using a colorimetric assay, and compounds 3 and 4 demonstrated interesting activity against PTP1B. |
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