| Synthesis of three bromophenols from red algae as PTP1B inhibitors | |
Guo Shuju1,2; Li Jing1 ; Li Ting1,2; Shi Dayong1; Han Lijun1
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| 2011 | |
| 发表期刊 | CHINESE JOURNAL OF OCEANOLOGY AND LIMNOLOGY
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| ISSN | 0254-4059 |
| 卷号 | 29期号:1页码:68-74 |
| 文章类型 | Article |
| 摘要 | 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, 3,4-dibromo-5-(2'-bromo-3',4'-dihydroxy-6'-methoxymethyl-benzyl)-benzene-1,2-diol (compound 9), 3,4-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.; 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, 3,4-dibromo-5-(2'-bromo-3',4'-dihydroxy-6'-methoxymethyl-benzyl)-benzene-1,2-diol (compound 9), 3,4-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. |
| 关键词 | Bromophenols Synthesis Ptp1b Inhibitory Activity |
| 学科领域 | Marine & Freshwater Biology ; Oceanography |
| DOI | 10.1007/s00343-011-9996-7 |
| URL | 查看原文 |
| 收录类别 | SCI |
| 语种 | 英语 |
| WOS记录号 | WOS:000286203200009 |
| 引用统计 | |
| 文献类型 | 期刊论文 |
| 条目标识符 | http://ir.qdio.ac.cn/handle/337002/12045 |
| 专题 | 海洋生物技术研发中心 实验海洋生物学重点实验室 |
| 作者单位 | 1.Chinese Acad Sci, Inst Oceanol, Qingdao 266071, Peoples R China 2.Chinese Acad Sci, Grad Univ, Beijing 100049, Peoples R China |
| 第一作者单位 | 中国科学院海洋研究所 |
| 推荐引用方式 GB/T 7714 | Guo Shuju,Li Jing,Li Ting,et al. Synthesis of three bromophenols from red algae as PTP1B inhibitors[J]. CHINESE JOURNAL OF OCEANOLOGY AND LIMNOLOGY,2011,29(1):68-74. |
| APA | Guo Shuju,Li Jing,Li Ting,Shi Dayong,&Han Lijun.(2011).Synthesis of three bromophenols from red algae as PTP1B inhibitors.CHINESE JOURNAL OF OCEANOLOGY AND LIMNOLOGY,29(1),68-74. |
| MLA | Guo Shuju,et al."Synthesis of three bromophenols from red algae as PTP1B inhibitors".CHINESE JOURNAL OF OCEANOLOGY AND LIMNOLOGY 29.1(2011):68-74. |
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