3-bromo-5-formyl-6-hydroxybenzoic acid | 134948-41-7

• 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-5-formyl-6-hydroxybenzoic acid
• 英文别名: 5-bromo-3-formyl-2-hydroxybenzoic acid；5-bromo-3-formylsalicyclic acid
• CAS: 134948-41-7
• 化学式: C₈H₅BrO₄
• 分子量: 245.029
• InChiKey: AZIOXDIHGGRKGS-UHFFFAOYSA-N

物化性质

• 熔点：
  204-206 °C
• 沸点：
  347.1±42.0 °C(Predicted)
• 密度：
  1.910±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-bromo-5-formyl-6-hydroxybenzoic acid 在 sodium hydroxide 、 sodium tetrahydroborate 、 硫酸 、 锌 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 16.0h， 生成 1,1-bis[3-chloro-3',5-carbonxy=2,4'-dihydroxydiphenyl]methane
  参考文献：
  名称：

  Synthesis and Anti-HIV Activity of Cosalane Analogues with Substituted Benzoic Acid Rings Attached to the Pharmacophore through Methylene and Amide Linkers

  摘要：

  The cosalane pharmacophore has been extended by the attachment of two additional substituted benzoic acid rings through amide and methylene linkers. The resulting compounds display significant antiviral activity when tested in vitro for inhibition of the cytopathic effects of HIV-1(RF) in CEM-SS cells and HIV-1(IIIB) in MT-4 cells. The compound containing the methylene linker also shows moderate activity versus HIV-2(ROD) in MT-4 cells. Because cosalane and related compounds containing extended pharmacophores inhibit the binding of gp120 to CD4, the presently described new compounds are assumed to act by a similar mechanism. A hypothetical model is proposed for the binding of the methylene-linked compound to CD4.

  DOI：

  10.1021/jo990177f
• 作为产物：
  描述：

  3-醛基水杨酸 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以90%的产率得到3-bromo-5-formyl-6-hydroxybenzoic acid
  参考文献：
  名称：

  Synthesis, biological evaluation and 3D-QSAR studies of 3-keto salicylic acid chalcones and related amides as novel HIV-1 integrase inhibitors

  摘要：

  HIV-1 integrase is one of the three most important enzymes required for viral replication and is therefore an attractive target for anti retroviral therapy. We herein report the design and synthesis of 3-keto salicylic acid chalcone derivatives as novel HIV-1 integrase inhibitors. The most active compound, 5-bromo-2-hydroxy-3-[3-(2,3,6-trichlorophenyl)acryloyl] benzoic acid (25) was selectively active against integrase strand transfer, with an IC50 of 3.7 mu M. While most of the compounds exhibited strand transfer selectivity, a few were nonselective, such as 5-bromo-3-[3-(4-bromophenyl)acryloyl]-2-hydroxybenzoic acid (15), which was active against both 3'-processing and strand transfer with IC50 values of 11 +/- 4 and 5 +/- 2 mu M, respectively. The compounds also inhibited HIV replication with potencies comparable with their integrase inhibitory potencies. Thus, 5-bromo-2-hydroxy-3-[3-(2,3,6-trichlorophenyl) acryloyl] benzoic acid (25) and 5-bromo-3-[3-(4-bromophenyl) acryloyl]-2-hydroxybenzoic acid (15) inhibited HIV-1 replication with EC50 values of 7.3 and 8.7 mu M, respectively. A PHASE pharmacophore hypothesis was developed and validated by 3D-QSAR, which gave a predictive r(2) of 0.57 for an external test set of ten compounds. Phamacophore derived molecular alignments were used for CoMFA and CoMSIA 3D-QSAR modeling. CoMSIA afforded the best model with q(2) and r(2) values of 0.54 and 0.94, respectively. This model predicted all the ten compounds of the test set within 0.56 log units of the actual pIC(50) values; and can be used to guide the rational design of more potent novel 3-keto salicylic acid integrase inhibitors (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.01.047

文献信息

• Tenacic Acids: A New Class of Tenacious Binders to Metal Oxide Surfaces
  作者：Rajesh Komati、Carl A. Mitchell、Anastasia LeBeaud、Huy Do、Galina Z. Goloverda、Vladimir L. Kolesnichenko

  DOI：10.1002/chem.201803242

  日期：2018.10.1

  The backbone of 2‐hydroxyisophthalic acid was identified as a potential metal oxide anchor because of the perfect alignment of all three of its donor groups for binding to inorganic surfaces. It can therefore be used in the design of organic linkers for metal oxide based hybrid materials. Optimized and scalable methods for the synthesis of 2‐hydroxyisophthalic acid (1) and its 5‐substituted derivatives:

  2-羟基间苯二甲酸的主链被认为是一种潜在的金属氧化物锚，因为它的所有三个供体基团完美排列以与无机表面结合。因此，它可用于金属氧化物基杂化材料的有机连接体的设计。用于合成 2-羟基间苯二甲酸 ( 1 ) 及其 5-取代衍生物：5-溴-( 2 )、5-磺氧基-( 3 )、5-羟基-( 4 ) 和 5-PEG600的优化且可扩展的方法( 5 ) 提出。动态光散射 (DLS) 表明，当用 NaOH 滴定 Fe III 水溶液时，化合物 2抑制Fe (OH) 3沉淀，而在结构相关的间苯二甲酸和水杨酸存在下进行类似的滴定，两者都缺少第三个供体基团， pH 值分别低至 2.3 和 3.5 时显示出浊度。由4.5 nm γ-Fe 2 O 3纳米粒子和5合成的加合物可溶于水、醇和CH 2 Cl 2，并在pH值4.4-8.7范围内形成稳定的水胶体。此外，在接近中性的 pH 值下，这些胶体可以在 100°C 下存活，这证明了
• A Novel Selective Oxidation of 5-Substituted 2-Hydroxy-3-hydroxymethylbenzaldehydes
  作者：Yuefei Hu、Hongwen Hu

  DOI：10.1055/s-1991-26458

  日期：——

  5-Substituted 2-hydroxy-1,3-benzenedicarbaldehydes 3 and 5-substituted 3-formyl-2-hydroxybenzoic acids 4 were prepared by selective oxidation of 5-substituted 2-hydroxy-3-(hydroxymethyl)-benzaldehydes 1 in a one-pot reaction. Compounds 1 were reacted with ethylenediamine and copper acetate to produce the complexes 2 as intermediates, in which formyl and phenolic hydroxy groups were protected in the subsequent oxidation step.

  5-取代的2-羟基-1,3-苯二甲醛3和5-取代的3-甲酰基-2-羟基苯甲酸4是通过在一锅反应中选择性氧化5-取代的2-羟基-3-(羟甲基)苯甲醛1制备的。化合物1与乙二胺和乙酸铜反应，生成中间体络合物2，其中羧基和酚羟基在随后的氧化步骤中得到了保护。
• FUSED RING HETEROCYCLE KINASE MODULATORS
  申请人：Arnold D. William

  公开号：US20070287711A1

  公开（公告）日：2007-12-13

  The present invention provides novel fused ring heterocycle kinase modulators and methods of using the novel fused ring heterocycle kinase modulators to treat diseases mediated by kinase activity.

  本发明提供了新型的融合环杂环激酶调节剂及其使用方法，用于治疗由激酶活性介导的疾病。
• Fused Ring Heterocycle Kinase Modulators
  申请人：Arnold William D.

  公开号：US20100036118A1

  公开（公告）日：2010-02-11

  The present invention provides novel fused ring heterocycle kinase modulators and methods of using the novel fused ring heterocycle kinase modulators to treat diseases mediated by kinase activity.

  本发明提供了新型融合环杂环激酶调节剂和使用这些新型融合环杂环激酶调节剂治疗由激酶活性介导的疾病的方法。
• Fused ring heterocycle kinase modulators
  申请人：SGX Pharmaceuticals, Inc.

  公开号：US08268994B2

  公开（公告）日：2012-09-18

  The present invention provides novel fused ring heterocycle kinase modulators and methods of using the novel fused ring heterocycle kinase modulators to treat diseases mediated by kinase activity.

  本发明提供了新型融合环杂环激酶调节剂以及使用这些新型融合环杂环激酶调节剂治疗由激酶活性介导的疾病的方法。