| Synthesis and protein tyrosine phosphatase 1B inhibition activities of two new synthetic bromophenols and their methoxy derivatives | |
| Cui Yongchao2; Shi Dayong1; Hu Zhiqiang1,2 | |
| 2011-11-01 | |
| 发表期刊 | CHINESE JOURNAL OF OCEANOLOGY AND LIMNOLOGY
 |
| ISSN | 0254-4059 |
| 卷号 | 29期号:6页码:1237-1242 |
| 文章类型 | Article |
| 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 (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.; 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. |
| 关键词 | Protein Tyrosine Phosphatase 1b Inhibition Bromophenol Derivatives Synthesis |
| 学科领域 | Marine & Freshwater Biology ; Oceanography |
| DOI | 10.1007/s00343-011-0271-8 |
| URL | 查看原文 |
| 收录类别 | SCI |
| 语种 | 英语 |
| WOS记录号 | WOS:000299039400010 |
| 引用统计 | |
| 文献类型 | 期刊论文 |
| 条目标识符 | http://ir.qdio.ac.cn/handle/337002/12043 |
| 专题 | 海洋生物技术研发中心 |
| 作者单位 | 1.Chinese Acad Sci, Inst Oceanol, Qingdao 266071, Peoples R China 2.Qingdao Univ Sci & Technol, Coll Chem & Mol Engn, Qingdao 266042, Peoples R China |
| 推荐引用方式 GB/T 7714 | Cui Yongchao,Shi Dayong,Hu Zhiqiang. Synthesis and protein tyrosine phosphatase 1B inhibition activities of two new synthetic bromophenols and their methoxy derivatives[J]. CHINESE JOURNAL OF OCEANOLOGY AND LIMNOLOGY,2011,29(6):1237-1242. |
| APA | Cui Yongchao,Shi Dayong,&Hu Zhiqiang.(2011).Synthesis and protein tyrosine phosphatase 1B inhibition activities of two new synthetic bromophenols and their methoxy derivatives.CHINESE JOURNAL OF OCEANOLOGY AND LIMNOLOGY,29(6),1237-1242. |
| MLA | Cui Yongchao,et al."Synthesis and protein tyrosine phosphatase 1B inhibition activities of two new synthetic bromophenols and their methoxy derivatives".CHINESE JOURNAL OF OCEANOLOGY AND LIMNOLOGY 29.6(2011):1237-1242. |
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