3-bromo-4-(2,3-dibromo-4,5-dihydroxybenzyl)-5-methoxymethylpyrocatechol | 65487-77-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-bromo-4-(2,3-dibromo-4,5-dihydroxybenzyl)-5-methoxymethylpyrocatechol
• 英文别名: 5-(2-bromo-3,4-dihydroxy-6-(methoxymethyl) benzyl)-3,4-dibromobenzene-1,2-diol；3-Bromo-4-(2,3-dibromo-4,5-dihydroxybenzyl)-5-methoxymethyl-pyrocatechol；3,4-dibromo-5-[[2-bromo-3,4-dihydroxy-6-(methoxymethyl)phenyl]methyl]benzene-1,2-diol
• CAS: 65487-77-6
• 化学式: C₁₅H₁₃Br₃O₅
• 分子量: 512.977
• InChiKey: IPYUYPHYIFALPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-bromo-4-(2,3-dibromo-4,5-dihydroxybenzyl)-5-methoxymethylpyrocatechol 、 硫酸二甲酯 在 potassium carbonate 作用下， 生成 2,3-dibromo-1-(2-bromo-3,4-dimethoxy-6-(methoxymethyl)benzyl)-4,5-dimethoxybenzene
  参考文献：
  名称：

  TWO NEW BROMOPHENOLS FROM THE RED ALGA,RHODOMELA LARIX

  摘要：

  从红藻Rhodomela larix中分离出两种新的溴代酚：2,2′,3,3′-四溴-4,4′,5,5′-四羟基二苯甲烷和2,2′,3-三溴-3′,4,4′,5-四羟基-6′-甲氧基甲基二苯甲烷。

  DOI：

  10.1246/cl.1977.1435
• 作为产物：
  描述：

  1-溴-2,3-二甲氧基-5-甲基苯 在 aluminum (III) chloride 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 磷酸 、 水 、 三溴化硼 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 四氯化碳 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 3-bromo-4-(2,3-dibromo-4,5-dihydroxybenzyl)-5-methoxymethylpyrocatechol
  参考文献：
  名称：

  Discovery of novel bromophenol 3,4-dibromo-5-(2-bromo-3,4-dihydroxy-6-(isobutoxymethyl)benzyl)benzene-1,2-diol as protein tyrosine phosphatase 1B inhibitor and its anti-diabetic properties in C57BL/KsJ-db/db mice

  摘要：

  In an effort to develop novel small molecule PTP1B inhibitors, a series of bromophenol derivatives were designed, synthesized and evaluated in vitro and in vivo. All of the synthesized compounds displayed weak to potent PTP1B inhibitory activities (5.62-9625%) at 20 mu g/mL. Among these compounds, 3,4-dibromo-5-(2-bromo-3,4-dihydroxy-6-(isobutoxymethyl)benzyl)benzene-1,2-diol (9) exhibited enhanced PTP1B inhibitory activity (IC50 = 1.50 mu M) than the lead compound BDDPM (IC50 = 2.42 mu M) and high selectivity against other PTPs (TCPTP, LAR, SHP-1 and SHP-2). Results of anti-diabetic assay using C57BL/KsJ-db/db mouse model demonstrated that compound 9 was effective at lowering blood glucose, total cholesterol and HbA1c (P < 0.01). (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.037

文献信息

• 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
  作者：Yusuf Akbaba、Halis Türker Balaydın、Süleyman Göksu、Ertan Şahin、Abdullah Menzek

  DOI：10.1002/hlca.200900300

  日期：——

  4‐Dibromo‐5‐[2‐bromo‐3,4‐dihydroxy‐6‐(methoxymethyl)benzyl]benzene‐1,2‐diol (2), a natural product, has been synthesized for the first time starting from (3‐bromo‐4,5‐dimethoxyphenyl)methanol (5) in five steps and with an overall yield of 34%. The reaction of some methoxymethyl‐substituted aryl methyl ethers with BBr3, followed by the addition of MeOH, afforded the corresponding methoxymethyl‐substituted arylphenols

  天然产物3,4-二溴-5- [2-溴-3,4-二羟基-6-（甲氧基甲基）苄基]苯1,2-二醇（2）首次从（3-溴-4,5-二甲氧基苯基）甲醇（5）分五个步骤，总产率为34％。一些甲氧基甲基取代的芳基甲基醚与BBr 3的反应，然后添加MeOH，可以高收率得到相应的甲氧基甲基取代的芳基酚。
• Discovery of novel bromophenol 3,4-dibromo-5-(2-bromo-3,4-dihydroxy-6-(isobutoxymethyl)benzyl)benzene-1,2-diol as protein tyrosine phosphatase 1B inhibitor and its anti-diabetic properties in C57BL/KsJ-db/db mice
  作者：Bo Jiang、Shuju Guo、Dayong Shi、Chao Guo、Tao Wang

  DOI：10.1016/j.ejmech.2013.03.037

  日期：2013.6

  In an effort to develop novel small molecule PTP1B inhibitors, a series of bromophenol derivatives were designed, synthesized and evaluated in vitro and in vivo. All of the synthesized compounds displayed weak to potent PTP1B inhibitory activities (5.62-9625%) at 20 mu g/mL. Among these compounds, 3,4-dibromo-5-(2-bromo-3,4-dihydroxy-6-(isobutoxymethyl)benzyl)benzene-1,2-diol (9) exhibited enhanced PTP1B inhibitory activity (IC50 = 1.50 mu M) than the lead compound BDDPM (IC50 = 2.42 mu M) and high selectivity against other PTPs (TCPTP, LAR, SHP-1 and SHP-2). Results of anti-diabetic assay using C57BL/KsJ-db/db mouse model demonstrated that compound 9 was effective at lowering blood glucose, total cholesterol and HbA1c (P < 0.01). (C) 2013 Elsevier Masson SAS. All rights reserved.
• TWO NEW BROMOPHENOLS FROM THE RED ALGA,<i>RHODOMELA LARIX</i>
  作者：Kazuya Kurata、Takashi Amiya

  DOI：10.1246/cl.1977.1435

  日期：1977.12.5

  Two new bromophenols, 2,2′,3,3′-tetrabromo-4,4′,5,5′-tetrahydroxydiphenylmethane and 2,2′,3-tribromo-3′,4,4′,5-tetrahydroxy-6′-methoxymethyldiphenylmethane have been isolated from the red alga, Rhodomela larix.

  从红藻Rhodomela larix中分离出两种新的溴代酚：2,2′,3,3′-四溴-4,4′,5,5′-四羟基二苯甲烷和2,2′,3-三溴-3′,4,4′,5-四羟基-6′-甲氧基甲基二苯甲烷。