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

Yongchao Cui; Dayong Shi; Zhiqiang Hu

doi:10.1007/s00343-011-0271-8

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

OriginalPaper | Updated：2023-05-16

- Synthesis and protein tyrosine phosphatase 1B inhibition activities of two new synthetic bromophenols and their methoxy derivatives
- Synthesis and protein tyrosine phosphatase 1B inhibition activities of two new synthetic bromophenols and their methoxy derivatives
- 海洋湖沼学报（英文） 2011年29卷第6期页码：1237-1242
- Affiliations：
  
  1. College of Chemistry and Molecular Engineering Qingdao University of Science and Technology
  2. Institute of Oceanology Chinese Academy of Sciences
- Author bio：
- Funds：
  
  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), and the Program of Qingdao Shinan District (No. 2009-HY-2-14)
- DOI：10.1007/s00343-011-0271-8
  中图分类号：
- 网络首发：2011-10-25，
  
  纸质出版：2011
- Accepted：
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Synthesis and protein tyrosine phosphatase 1B inhibition activities of two new synthetic bromophenols and their methoxy derivatives[J]. 海洋湖沼学报（英文）, 2011,29(6):1237-1242.

Cui, Y., Shi, D. & Hu, Z. Synthesis and protein tyrosine phosphatase 1B inhibition activities of two new synthetic bromophenols and their methoxy derivatives., Chin. J. Ocean. Limnol. 29, 1237–1242 (2011). https://doi.org/10.1007/s00343-011-0271-8
Synthesis and protein tyrosine phosphatase 1B inhibition activities of two new synthetic bromophenols and their methoxy derivatives[J]. 海洋湖沼学报（英文）, 2011,29(6):1237-1242. DOI： 10.1007/s00343-011-0271-8.

Cui, Y., Shi, D. & Hu, Z. Synthesis and protein tyrosine phosphatase 1B inhibition activities of two new synthetic bromophenols and their methoxy derivatives., Chin. J. Ocean. Limnol. 29, 1237–1242 (2011). https://doi.org/10.1007/s00343-011-0271-8 DOI：

摘要

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)

3-dibromo-1-(2′-bromo-6′-(2″-bromo-4″

5″-dimethoxybenzyl)-3′

4′-dimethoxybenzyl)-4

5-dimethoxybenzene (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.

关键词

Keywords

references

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