中国科学院机构知识库网格
Chinese Academy of Sciences Institutional Repositories Grid
首页 机构 成果 学者
  
  1. CAS IR Grid
  2. 海洋研究所
  3. 中国科学院海洋研究所
  4. 海洋生物技术研发中心
Synthesis of three bromophenols from red algae as PTP1B inhibitors

文献类型：期刊论文

作者Guo Shuju1,2; Li Jing1; Li Ting1,2; Shi Dayong1; Han Lijun1
刊名CHINESE JOURNAL OF OCEANOLOGY AND LIMNOLOGY
出版日期2011
卷号29期号:1页码:68-74
关键词Bromophenols Synthesis Ptp1b Inhibitory Activity
ISSN号0254-4059
DOI10.1007/s00343-011-9996-7
文献子类Article
英文摘要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.
学科主题Marine & Freshwater Biology ; Oceanography
URL标识查看原文
语种英语
WOS记录号WOS:000286203200009
公开日期2012-07-03
源URL[http://ir.qdio.ac.cn/handle/337002/12046]  
专题海洋研究所_海洋生物技术研发中心
海洋研究所_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
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.

入库方式： OAI收割

来源：海洋研究所

浏览0
下载0
收藏0
其他版本

除非特别说明，本系统中所有内容都受版权保护，并保留所有权利。