2-(5-bromo-2-hydroxylbenzylideneamino)benzoic acid | 57039-60-8

• 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-(5-bromo-2-hydroxylbenzylideneamino)benzoic acid
• 英文别名: N-(2-carboxyphenyl)-5'-bromosalicylidenimine；(5-bromo-salicylidene)-anthranilic acid；2-(5-bromo-2-hydroxy-benzylideneamino)-benzoic acid；N-(5-bromo-2-hydroxy-benzyliden)-anthranilic acid；N-(5-Brom-2-hydroxy-benzyliden)-anthranilsaeure；N-(2-Carboxyphenyl)-5-brom-salicylaldimin；Benzoic acid, 2-[[(5-bromo-2-hydroxyphenyl)methylene]amino]-；2-[(5-bromo-2-hydroxyphenyl)methylideneamino]benzoic acid
• CAS: 57039-60-8
• 化学式: C₁₄H₁₀BrNO₃
• 分子量: 320.142
• InChiKey: NQGZOBSSPFKBAH-UHFFFAOYSA-N

物化性质

• 沸点：
  525.5±50.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(5-bromo-2-hydroxylbenzylideneamino)benzoic acid 生成 (13E,13'E)-2,2'-dibromo-[6,6']spirobi(dibenzo[d,h][1,3,7,2]dioxazasilecine)-8,8'-dione
  参考文献：
  名称：

  Chavan,S.N. et al., Indian Journal of Chemistry, 1975, vol. 13, p. 808 - 811

  摘要：

  DOI：
• 作为产物：
  描述：

  邻氨基苯甲酸 、 5-溴水杨醛 以 乙醇 为溶剂， 反应 3.0h， 以74%的产率得到2-(5-bromo-2-hydroxylbenzylideneamino)benzoic acid
  参考文献：
  名称：

  Synthesis and evaluation of copper complexes of Schiff-base condensates from 5-substituted-2-hydroxybenzaldehyde and 2-substituted-benzenamine as selective inhibitors of protein tyrosine phosphatases

  摘要：

  Five copper complexes, [Cu(bhbb,chbb,ohbb)(H2O)(n)] (tridentate-ligands: H(2)bhbb = 2-(5-bromo-2-hydroxylbenzylideneamino)benzoic acid, 1; H(2)chbb = 2-(5-chloro-2-hydroxylbenzylideneamino)benzoic acid, 2; H(2)nhbb = 2-(5-nitro-2-hydroxyl-benzylideneamino)benzoic acid, 3) and [Cu(cpmp,npmp)(2)] (bidentate-ligands: Hcpmp = 4-chloro-2-((phenylimino)methyl)phenol, 4; Hnpmp = 4-bromo-2-((phenyl-imino)methyl)phenol, 5) have been prepared and characterized by EA, IR, EPR UV-Vis, and ESI-MS. Structure-activity relationship of copper complexes in inhibiting protein tyrosine phosphatases (protein tyrosine phosphatase 1B, PTP1B; T-cell protein tyrosine phosphatase, TCPTP; megakaryocyte protein-tyrosine phosphatase, PTP-MEG2; Src homology phosphatase 1, SHP-1 and Src homology phosphatase 2, SHP-2) is investigated. Inhibitory activities of complexes against the five PTPs indicate that they potently inhibit PTP1B, TCPTP, PTP-MEG2 and SHP-1, but do not inhibit SHP-2. In the complexes, 5 exhibits very strong inhibition (IC50, 0.059 mu M) and better selectivity against PTP1B while 1 and 2 show very strong inhibition (IC50 = 0.089 and 0.067 mu M) and a little selectivity against TCPTP. Compared with the oxovanadium(IV) complexes of same ligands, the copper complexes increase the inhibitory ability against TCPTP, PTP-MEG2 and SHP-1 but decrease the inhibition against SHP-2. For complex 5, the inhibition over PTP1B, TCPTP, PTP-MEG2 and SHP-1 are all improved about 5- to 15-fold compared with the oxovanadium(IV) complex. The results demonstrate that both the ligand structures and the center metals influence the inhibition and selectivity against different PTPs. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2013.05.018

文献信息

• Synthesis and characterization of vanadyl(IV) complexes of Schiff bases derived from anthranilic acid and salicylaldehyde (or its derivatives) or acetylacetone. Single crystal X-ray structures of the oxidized products
  作者：Gebray Asgedom、Alavattam Sreedhara、Jussi Kivikoski、Chebrolu P. Rao

  DOI：10.1016/0277-5387(96)00304-x

  日期：1997.1

  dimeric vanadyl(IV) complexes of Schiff bases derived from [1+1] condensation of salicylaldehyde (or its derivatives) and anthranilic acid, have been synthesized from CH3CN and were characterized by elemental analysis, FTIR, EPR, absorption, TGA, cyclic voltammetry and room temperature magnetic susceptibility measurements. These complexes were found to be oxidized by air in polar solvents like MeOH and DMF

  由CH 3 CN合成了由水杨醛（或其衍生物）和邻氨基苯甲酸的[1 + 1]缩合衍生的席夫碱无水二聚钒（IV）配合物，并通过元素分析，FTIR，EPR，吸收， TGA，循环伏安法和室温磁化率测量。发现这些络合物在极性溶剂（如MeOH和DMF）中被空气氧化为V V产物。该Ë 1/2发现该值约为660mV，表明与烷氧基键合的钒配合物相比，car☐ylate基团更有利于钒（IV）结合。这些络合物的氧化不稳定性取决于水杨醛环上的取代基，并遵循在MeOH和DMF中的5，6-苯并> H 3 3-OMe顺序。试图从吡啶中重结晶二聚钒（IV）配合物导致氧化，聚合和席夫碱配体损失的产物。X射线单晶衍射表明，氧化产物为带有吡啶鎓抗衡阳离子的十钒酸盐，[C 5 NH 6 ] 6 V 10 O 28 ·2H 2。O.当从MeOH中重结晶双核钒基（IV）配合物时，会得到单核碳酰化合八面体VO 3+部分的单核产物，以及
• Schiff base oxovanadium complexes resist the assembly behavior of human islet amyloid polypeptide
  作者：Jufei Xu、Gehui Gong、Xiangyi Huang、Weihong Du

  DOI：10.1016/j.jinorgbio.2018.05.006

  日期：2018.9

  peptides, and metal complexes. Vanadium complexes have been applied for the treatment of diabetes since the 19th century. However, the antidiabetes mechanism remains unclear. In this work, we used four Schiff base oxidovanadium(IV) complexes, namely VO(bhbb)·H2O (1, and ligand 1 H2bhbb, 2-(5-bromo-2-hydroxylbenzylideneamino) benzoic acid), VO(nhbb)·H2O (2, and lignad 2 H2nhbb, 2-(5-nitro-2-hydroxylbenzylideneamino)

  人胰岛淀粉样多肽（hIAPP）的错误折叠和原纤维化与II型糖尿病（T2DM）的病理过程有关。hIAPP聚集的抑制剂包括芳香族有机分子，短肽和金属络合物。自19世纪以来，钒配合物已被用于治疗糖尿病。但是，抗糖尿病机制仍不清楚。在这项工作中，我们使用了四种席夫碱氧化钒（IV）配合物，即VO（bhbb）·H2O（1和配体1 H2bhbb，2-（5-溴-2-羟基苄基亚氨基）苯甲酸），VO（nhbb）· H2O（2和Lignad 2 H2nhbb，2-（5-硝基-2-羟基苄叉亚氨基）苯甲酸），VO（cpmp）2（3和配体3 Hcpmp，4-氯-2-（苯基亚氨基）甲基）苯酚） ，VO（bpmp）2（4和配体4 Hbpmp，4-溴-2-（苯氨基）甲基）苯酚）抑制hIAPP的原纤维形成并减少肽诱导的细胞毒性。结果表明，四种席夫碱氧化钒配合物有效地阻碍了hIAPP的聚集并将成熟的原纤维分解为单体或低聚物。这
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Cu: MVol.B4, 169, page 1821 - 1824
  作者：

  DOI：——

  日期：——
• Agarwal, A. K.; Kumar, R.; Singh, N., 1980, vol. 27, p. 31 - 35
  作者：Agarwal, A. K.、Kumar, R.、Singh, N.、Kansal, B. D.

  DOI：——

  日期：——
• Muto, Y., Bulletin of the Chemical Society of Japan, 1960, vol. 33, p. 1242 - 1247
  作者：Muto, Y.

  DOI：——

  日期：——