Synthesis of three bromophenols from red algae as PTP1B inhibitors

Shuju Guo; Jing Li; Ting Li; Dayong Shi; Lijun Han

doi:10.1007/s00343-011-9996-7

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Synthesis of three bromophenols from red algae as PTP1B inhibitors

OriginalPaper | Updated：2023-05-16

- Synthesis of three bromophenols from red algae as PTP1B inhibitors
- Synthesis of three bromophenols from red algae as PTP1B inhibitors
- 海洋湖沼学报（英文） 2011年29卷第1期页码：68-74
- Affiliations：
  
  1. Institute of Oceanology Chinese Academy of Sciences
  2. Graduate University of the Chinese Academy of Sciences
- Author bio：
- Funds：
  
  Supported by the National Major Research Program of China (No. 2009ZX09103-148) and the National High Technology Research and Development Program of China (863 program) (Nos. 2007AA09Z410, 2007AA091604)
- DOI：10.1007/s00343-011-9996-7
  中图分类号：
- 网络首发：2011-01-15，
  
  纸质出版：2011
- Accepted：
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Synthesis of three bromophenols from red algae as PTP1B inhibitors[J]. 海洋湖沼学报（英文）, 2011,29(1):68-74.

Guo, S., Li, J., Li, T. et al. Synthesis of three bromophenols from red algae as PTP1B inhibitors., Chin. J. Ocean. Limnol. 29, 68–74 (2011). https://doi.org/10.1007/s00343-011-9996-7
Synthesis of three bromophenols from red algae as PTP1B inhibitors[J]. 海洋湖沼学报（英文）, 2011,29(1):68-74. DOI： 10.1007/s00343-011-9996-7.

Guo, S., Li, J., Li, T. et al. Synthesis of three bromophenols from red algae as PTP1B inhibitors., Chin. J. Ocean. Limnol. 29, 68–74 (2011). https://doi.org/10.1007/s00343-011-9996-7 DOI：

摘要

Abstract

Bromophenols are a set of natural products widely distributed in seaweed

most of which exhibit interesting and useful biological activities. To develop a reliable and efficient synthetic route to these natural bromophenols

three of them

4-dibromo-5-(2′-bromo-3′

4′-dihydroxy-6′-methoxymethyl-benzyl)-benzene-1

2-diol (compound 9)

4-dibromo-5-(2′-bromo-6′-ethoxy methyl-3′

4′-dihydroxybenzyl)-benzene-1

2-diol (compound 10)

and 3-bromo-4-(3′-bromo-4′

5′-dihydroxy benzyl)-5-(ethoxymethyl)-benzene-1

2-diol (compound 14)

isolated from red marine algae

have been synthesized in eight steps with an overall yield of 14.4%

14.4%

and 18.2% respectively

via a practical approach employing bromination

Wolff-Kishner-Huang reduction and a Friedel-Crafts reaction as key steps. The protein tyrosine phosphatase 1B (PTP1B) inhibitory activities of the synthetic compounds were evaluated by the colorimetric assay. The results show that these compounds are moderate PTP1B inhibitors. The synthesis of these bromophenol derivatives makes in vivo studies of their structure-activity relationships and inhibition activity against PTP1B possible.

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references

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