Synthesis and protein tyrosine phosphatase 1B inhibition activities of two new synthetic bromophenols and their methoxy derivatives

• Published in: Chinese journal of oceanology and limnology Vol. 29; no. 6; pp. 1237 - 1242
• Main Authors: Cui, Yongchao, Shi, Dayong, Hu, Zhiqiang
• Format: Journal Article
• Language: English
• Published: Heidelberg SP Science Press 01.11.2011; Springer Nature B.V
• Subjects: Algae; Biology; Catechol; Colorimetry; Earth and Environmental Science; Earth Sciences; Enzymes; Ionization; Marine; Marine biology; Mass spectrometry; Mass spectroscopy; NMR; Nuclear magnetic resonance; Oceanography; Phosphatase; Protein biosynthesis; Protein synthesis; Protein-tyrosine-phosphatase; Proteins; Rhodomela confervoides; Tyrosine; Vanillin; synthesis; protein tyrosine phosphatase 1B inhibition; bromophenol derivatives
• ISSN: 0254-4059; 2096-5508; 1993-5005; 2523-3521
• DOI: 10.1007/s00343-011-0271-8

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 1 H NMR, 13 C 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.