2,2',3-tribromo-3',4,4',5-tetrahydroxy-6'-hydroxymethyldiphenyl methane

• 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: 2,2',3-tribromo-3',4,4',5-tetrahydroxy-6'-hydroxymethyldiphenyl methane
• 英文别名: 5-(2-bromo-3,4-dihydroxy-6-(hydroxymethyl)benzyl)-3,4-dibromobenzene-1,2-diol；3,4-Dibromo-5-[2-bromo-3,4-dihydroxy-6-(hydroxymethyl)benzyl]benzene-1,2-diol；3,4-dibromo-5-[[2-bromo-3,4-dihydroxy-6-(hydroxymethyl)phenyl]methyl]benzene-1,2-diol
• 化学式: C₁₄H₁₁Br₃O₅
• 分子量: 498.95
• InChiKey: FZJSRHWEUVKMLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  101
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2',3-tribromo-3',4,4',5-tetrahydroxy-6'-hydroxymethyldiphenyl methane 在 palladium/alumina 氢气 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以100%的产率得到4-[(3,4-Dihydroxyphenyl)methyl]-5-(hydroxymethyl)benzene-1,2-diol
  参考文献：
  名称：

  Antimicrobial activities of the bromophenols from the red alga Odonthalia corymbifera and some synthetic derivatives

  摘要：

  A series of bromophenols was obtained by isolation from red alga Odonthalia corymbifera and by reactions of bis(hydroxyphenyl)methanes with bromine. New bromophenols including 3,3,5,5'-tetrabromo-2,2',4,4'-tetrahydroxydiphenylmethane (10), a regioisomer of the potent antimicrobial natural product, together with known derivatives were synthesized in high yield. All of the isolated and synthesized compounds were tested for antimicrobial activity against Gram-negative, Gram-positive bacteria and fungi. The preliminary structure-activity relationship, to elucidate the essential structure requirements for antimicrobial activity, has been described. Among the isolated natural products 2,2',3,3'-tetrabromo-4,4',5,5'-tetrahydroxydiphenylmethane (4) was found to be the most active derivative against Candida albicans, Aspergillus fumigatus, Trichophyton rubrum, and Trichophyton mentagrophytes. The synthetic bromophenols 3,3'-dibromo-6,6'-dihydroxydiphenylmethane (13) and 3,3',5,5'-tetrabromo-6, 6'-dihydroxydiphenylmethane (14) showed potent antibacterial effect against Staphylococcus aureus, Bacillus subtilis, Micrococcus luteus. Proteus vulgaris, and Salmonella typhimurium. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.003
• 作为产物：
  描述：

  2,3-dibromo-1-(2-bromo-3,4-dimethoxy-6-(methoxymethyl)benzyl)-4,5-dimethoxybenzene 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 2,2',3-tribromo-3',4,4',5-tetrahydroxy-6'-hydroxymethyldiphenyl methane
  参考文献：
  名称：

  天然存在的3,4-二溴-5- [2-溴-3,4-二羟基-6-（甲氧基甲基）苄基]苯-1,2-二醇的生物活性和芳基甲基的区域选择性O-脱甲基化的全合成醚类

  摘要：

  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。

  DOI：

  10.1002/hlca.200900300

文献信息

• PTP1B INHIBITORS, SYNTHESIS THEREOF AND APPLICATION THEREOF IN PREPARATION OF MEDICAMENTS FOR TREATING TYPE 2 DIABETES MELLITUS
  申请人：Shi Dayong

  公开号：US20130131182A1

  公开（公告）日：2013-05-23

  The present invention relates to chemical total synthesis methods of six novel protein tyrosine phosphatase-1B (PTP1B) inhibitors and application of the inhibitors in the preparation of medicaments for treating type 2 diabetes mellitus (T2DM). The PTP1B inhibitors use one or more of the six compounds represented by the structural formulae 1, 2, 3, 4, 5 and 6, as active components. The compounds can enhance the sensitivity of an insulin receptor by inhibiting the activity of PTP1B, thereby having a favorable therapeutic effect on insulin-resistant T2DM.

  本发明涉及六种新型蛋白酪氨酸磷酸酶-1B（PTP1B）抑制剂的化学全合成方法，以及这些抑制剂在制备治疗2型糖尿病（T2DM）药物中的应用。PTP1B抑制剂使用由结构式1、2、3、4、5和6表示的六种化合物中的一种或多种作为活性成分。这些化合物可以通过抑制PTP1B的活性来增强胰岛素受体的敏感性，从而对胰岛素抵抗性T2DM具有良好的治疗效果。
• Cellular Antioxidant Effect of Four Bromophenols from the Red Algae, Vertebrata lanosa
  作者：Elisabeth Olsen、Espen Hansen、Johan Isaksson、Jeanette Andersen

  DOI：10.3390/md11082769

  日期：——

  Three known bromophenols, 2,3-dibromo-4,5-dihydroxybenzylaldehyde (1), 2,2′,3-tribromo-3′,4,4′,5-tetrahydroxy-6′-hydroxymethyldiphenylmethane (2) and bis(2, 3-dibromo-4,5-dihydroxylbenzyl) ether (3), and one new one, 5,5″-oxybis(methylene)bis (3-bromo-4-(2′,3′-dibromo-4′,5′-dihydroxylbenzyl)benzene-1,2-diol) (4), were isolated from an extract of the red alga, Vertebrata lanosa. The antioxidant activity of these four bromophenols was examined using one biochemical and two cellular assays: Oxygen Radical Absorbance Capacity (ORAC), Cellular Antioxidant Activity (CAA) and Cellular Lipid Peroxidation Antioxidant Activity (CLPAA) assays. Compound 2 distinguished itself by showing potent activity, having a better antioxidant effect than luteolin in both the CAA and CLPAA assays and of quercetin in the CLPAA assay. Although several bromophenols are known to be potent antioxidants in biochemical assays, this is the first time their cellular antioxidant activity has been demonstrated.

  三种已知的溴苯酚：2,3-二溴-4,5-二羟基苄醛（1）、2,2′,3-三溴-3′,4,4′,5-四羟基-6′-羟甲基二苯甲烷（2）和双（2,3-二溴-4,5-二羟基苄基）醚（3）、和双(2,3-二溴-4,5-二羟基苄基)醚(3)，以及一种新的 5,5″-氧双(亚甲基)双(3-溴-4-(2′,3′-二溴-4′,5′-二羟基苄基)苯-1,2-二醇)(4)是从红藻 Vertebrata lanosa 的提取物中分离出来的。这四种溴酚类化合物的抗氧化活性通过一种生化试验和两种细胞试验进行了检测：氧自由基吸收能力（ORAC）、细胞抗氧化活性（CAA）和细胞脂质过氧化抗氧化活性（CLPAA）测定。化合物 2 显示出了强大的活性，其抗氧化效果在 CAA 和 CLPAA 试验中均优于木犀草素，在 CLPAA 试验中优于槲皮素。虽然已知几种溴酚类化合物在生化试验中是强效抗氧化剂，但这是它们的细胞抗氧化活性首次得到证实。
• Bromophenols from the Red Alga <i>Rhodomela </i><i>c</i><i>onfervoides</i>
  作者：X. Fan、N.-J. Xu、J.-G. Shi

  DOI：10.1021/np020528c

  日期：2003.3.1

  5-dihydroxybenzyl) ether (12), 3-bromo-4-(2,3-dibromo-4,5-dihydroxybenzyl)-5-methoxymethylpyrocatechol (13), and 2,2',3,3'-tetrabromo-4,4',5,5'-tetrahydroxydiphenyl methane (14), were isolated from the red alga Rhodomela confervoides. Their structures were elucidated by chemical and spectroscopic methods including IR, HRFABMS, and 1D and 2D NMR techniques.

  从红藻Rhodomela confervoides中分离出了5-二羟基苄基）-5-甲氧基甲基邻苯二酚（13）和2,2'，3,3'-四溴-4,4'，5,5'-四羟基二苯甲烷（14）。通过化学和光谱学方法（包括IR，HRFABMS和1D和2D NMR技术）阐明了它们的结构。
• 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.
• US8816129B2
  申请人：——

  公开号：US8816129B2

  公开（公告）日：2014-08-26

表征谱图