摘要
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-(2p-bromo-6p-(3q,4q-dimethoxybenzyl)- 3p,4p-dimethoxybenzyl)-4,5-dimethoxybenzene(2),2,3-dibromo-1-(2p-bromo-6p-(2q-bromo-4q,5q-dimethoxy-benzyl)-3p,4p-dimethoxybenzyl)-4,5-dimethoxybenzene(3),3,4-dibromo-5-(2p-bromo-6p-(2q-bromo-4q,5q-dihydroxybenzyl)-3p,4p-dihydroxybenzyl)pyrocatechol(4)and 3,4-dibromo-5-(2p-bromo-6p-(3q,4q-dihydroxybenzyl)-3p,4p-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.
3-bromo-4,5-bis(2,3-dibromo-4,5-dihydroxybenzyl)-l,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 H 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 "-dimethoxy- benzyl)-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.
基金
Supported by the National Major Research Program of China"The Creation for Significant Innovative Drugs"(No.2009ZX09103-148)
the Natural Science Foundation of Shandong(No.BS2009YY011)
the Natural Science Foundation of Qingdao(No.10-3-4-8-2-JCH)
the Program of Qingdao Shinan District(No.2009-HY-2-14)