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

Your Location：

Home >

Browse articles >

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

Updated：2023-05-16

- Synthesis and protein tyrosine phosphatase 1B inhibition activities of two new synthetic bromophenols and their methoxy derivatives
- Journal of Oceanology and Limnology Vol. 29, Issue 6, Pages: 1237-1242(2011)
- 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：
- DOI：10.1007/s00343-011-0271-8
  CLC：
- Online First：25 October 2011，
  
  Published：2011
- Accepted：
Scan QR Code
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：

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

Akbaba Y, Balaydin H T, Goksu S, Sahin E, Menzek A. 2010. Total synthesis of the biologically active, naturally occurring 3,4-dibromo-5-[2-bromo-3,4-dihydroxy-6-(methoxymethyl)benzyl]benzene-1,2-diol and regioselective o-demethylation of aryl methyl ethers. Helv. Chim. Acta, 93(6): 1 127–1 135.

Balaydin H T, Akbaba Y, Menzek A, Sahin E, Goksu S. 2009. First and short syntheses of biologically active, naturally occurring brominated mono- and dibenzyl phenols. Arkivoc, XIV: 75–87.

Balaydin H T, Gulcin I, Menzek A, Goksu S, Sahin E. 2010. Synthesis and antioxidant properties of diphenylmethane derivative bromophenols including a natural product. J. Enzyme. Inhib. Med. Chem., 25(5): 685–695.

Blaskovich M A, Kim H O. 2002. Recent discovery and development of protein tyrosine phosphatase inhibitors. Expert Opin. Ther. Patents, 12(6): 871–905.

Choi J S, Park H J, Jung H A, Chung H Y, Jung J H, Choi W C. 2000. A cyclohexanonyl bromophenol from the red alga Symphyocladia latiuscula. J. Nat. Prod., 63(12): 1 705–1 706.

Fan X, Xu N J, Shi J G. 2003. Bromophenols from the red alga Rhodomela confervoides. J. Nat. Prod., 66(3): 455–458.

Ford P, Davidson B. 1993. Synthesis of varacin, a cytotoxic naturally occurring benzopentathiepin isolated from a marine ascidian. J. Org. Chem., 58(17): 4 522–4 523.

Furstner A, Stelzer F, Rumbo A, Krause H. 2002. Total synthesis of the turrianes and evaluation of their DNA-cleaving properties. Chem. Eur. J., 8(8): 1 856–1 871.

Hodgkin J H, Craigie J S, McInnes A G. 1966. The occurrence of 2,3-dibromobenzyl alcohol 4,5-disulfate, dipotassium salt, in Polysiphonia lanosa. Can. J. Chem., 44(1): 74–78.

Ma M, Zhao J L, Wang S J, Li S, Yang Y C, Shi H G, Fan X, He L. 2006. Bromophenols coupled with methyl gamma-ureidobutyrate and bromophenol sulfates from the red alga Rhodomela confervoides. J. Nat. Prod., 69(2): 206–210.

Oh K B, Lee J H, Lee J W, Yoon K M, Chung S C, Jeon H B, Shin J, Lee H S. 2009. Synthesis and antimicrobial activities of halogenated bis(hydroxyphenyl) methanes. Bioorg. Med. Chem. Lett., 19(3): 945–948.

Saltiel A R, Kahn C R. 2001. Insulin signalling and the regulation of glucose and lipid metabolism. Nature, 414(6 865): 799–806.

Shi D Y, Li J, Guo S J, Su H, Fan X. 2009. The antitumor effect of bromophenol derivatives in vitro and Leathesia nana extract in vivo. Chin. J. Oceanol. and Limnol., 27(2): 277–282.

Shi D Y, Xu F, He J, Li J, Fan X, Han L J. 2008. Inhibition of bromophenols against PTP1B and anti-hyperglycemic effect of Rhodomela confervoides extract in diabetic rats. Chin. Sci. Bull., 53(16): 2 476–2 479.

Shoeib N A, Bibby M C, Blunden G, Linley P A, Swaine D J, Wheelhouse R T, Wright C W. 2004. In-vitro cytotoxic activities of the major bromophenols of the red alga Polysiphonia lanosa and some novel synthetic isomers. J. Nat. Prod., 67(9): 1 445–1 449.

Srikrishna A, Satyanarayana G. 2006. Total synthesis of (+/-)-herbertenediol. Tetrahedron, 62(12): 2 892–2 900.

Shrikrishna D, Jonathan C. 2003. Protein-tyrosine phosphatase 1B as a potential drug target for obesity. Curr. Drug Targets Immune Endocr. Metabol. Disord., 3(4): 299–304.

Vickery E, Pahler L, Eisenbraun E. 1979. Selective O-demethylation of catechol ethers. Comparison of boron tribromide and iodotrimethylsilane. J. Org. Chem., 44(24): 4 444–4 446.

Xu N J, Fan X, Yang Y C, Shi J G. 2003. A new poly brominated dibenzylphenol from Rhodomela confervoides. Chin. Chem. Lett., 14(8): 807–809.

Xu X, Song F, Wang S, Li S, Xiao F, Zhao J, Yang Y, Shang S, Yang L, Shi J. 2004. Dibenzyl bromophenols with diverse dimerization patterns from the brown alga Leathesia nana. J. Nat. Prod., 67(10): 1 661–1 666.

Zabolotny J M, Bence-Hanulec K K, Stricker-Krongrad A, Haj F, Wang Y P, Minokoshi Y, Kim Y B, Elmquist J K, Tartaglia L A, Kahn B B, Neel B G. 2002. PTP1B regulates leptin signal transduction in vivo. Dev. Cell, 2(4): 489–495.

Zhao J L, Fan X, Wang S J, Li S A, Shang S Q, Yang Y C, Xu N J, Lu Y, Shi J G. 2004. Bromophenol derivatives from the red alga Rhodomela confervoides. J. Nat. Prod., 67(6): 1 032–1 035.

Zhao J L, Ma M, Wang S J, Li S, Cao P, Yang Y C, Lu Y, Shi J G, Xu N J, Fan X, He L. 2005. Bromophenols coupled with derivatives of amino acids and nucleosides from the red alga Rhodomela confervoides. J. Nat. Prod., 68(5): 691–694.

Views

Downloads

CSCD

Alert me when the article has been cited

Submit

Tools

Publicity Resources

Preparation of pure gum raw materials-low brown algae application

The antitumor effect of bromophenol derivatives in vitro and Leathesia nana extract in vivo

Synthesis, algal inhibition activities and QSAR studies of novel gramine compounds containing ester functional groups

Synthesis of three bromophenols from red algae as PTP1B inhibitors

PI Gain Scheduling Control for Flight EnvironmentSimulation System of Altitude Ground TestFacilities Based on LMI Pole Assignment

Related Author

LIU Boxiang

WANG Xiaomei

WANG Fahe

LI Kechang

LU Caiyuan

CHEN Yongfu

LIU Zhongdong

WAN Mengfei

Related Institution

Food Science and Technology, Henan University of Technology

Ruilin Chem. Ltd.

State Key Laboratory of Bioactive Seaweed Substances, Qingdao Brightmoon Seaweed Group Co. Ltd.

Lab, Stanford University

Education Ministry Key Laboratory of Marine Chemistry Theory and Technology Ocean University of China

Address：Editorial Office of JOL, 88 Haijun Rd. Qingdao, 266000, China
Tel：+86-532-82898754 Email：jol@qdio.ac.cn
Technical support is provided by Beijing Founder electronics co., LTD 京ICP备09064830号-19 京公网安备11010802024621
It is recommended to read the content of this site in Chrome&IE9+. Please switch to extreme mode in browser 360.
Cookies We use cookies to help provide and enhance our service and tailor content. By continuing, you agree to the use of cookies.

⁰