2-(2-羟基苯基)-3H-苯并咪唑-4-羧酸 | 904817-12-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 2-(2-羟基苯基)-3H-苯并咪唑-4-羧酸
• 英文名称: 2-(2-hydroxyphenyl)-1H-benzo[d]imidazole-4-carboxylic acid
• 英文别名: 2-(2-Hydroxy-phenyl)-3H-benzoimidazole-4-carboxylic acid；2-(2-hydroxyphenyl)-1H-benzimidazole-4-carboxylic acid
• CAS: 904817-12-5
• 化学式: C₁₄H₁₀N₂O₃
• 分子量: 254.245
• InChiKey: FCJWMWWRYMPNKR-UHFFFAOYSA-N

物化性质

• 熔点：
  310 °C (decomp)
• 沸点：
  575.6±56.0 °C(Predicted)
• 密度：
  1.483±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.2
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-(2-羟基苯基)-3H-苯并咪唑-4-羧酸 在 N-羟基丁二酰亚胺 、 N,N'-二环己基碳二亚胺 、 potassium hydroxide 作用下， 以 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  基于多奈哌齐的杂种作为多功能抗阿尔茨海默氏病螯合剂：位置异构化的影响

  摘要：

  阿尔茨海默氏病（AD）的复杂和多因素性质要求能够击中不同的病理生理的目标，如胆碱能功能障碍，淀粉样蛋白β（A存款化合物的开发β）肽和金属dyshomeostasis。为了继续寻找新的抗AD药物，在重新定位多奈哌齐（DNP）药物的基础上，通过将DNP部分的苄基哌啶模拟物与羟基苯基-苯并咪唑（BIM）螯合单元邻位连接，再次遵循了一种设计策略（化合物1）。在此，化合物1和位置异构体2在它们的潜在的多个性能方面相比：两者都存在良好乙酰胆碱酯酶（AChE）抑制（低微摩尔范围），并且A的中等/良好抑制剂β自和Cu介导的聚集，抑制过程为主要是由于配体之间插原纤维的β-折叠；化合物1对Cu 2+和Zn 2+的螯合能力（pCu = 14.3，pZn = 6.4，pH 7.4，C L / C M  = 10，C M  = 10 -6  M）具有比2（pCu = 10.7， pZn = 6.3），归因于其建立三

  DOI：

  10.1016/j.jinorgbio.2020.111039
• 作为产物：
  描述：

  methyl 2-[2-(benzyloxy)phenyl]-1H-benzimidazole-4-carboxylate 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 14.0h， 生成 2-(2-羟基苯基)-3H-苯并咪唑-4-羧酸
  参考文献：
  名称：

  Synthesis and anticancer evaluation of bis(benzimidazoles), bis(benzoxazoles), and benzothiazoles

  摘要：

  Four classes of UK-1 analogues were synthesized and their cytotoxicity testing against human A-549, BFTC-905, RD, MES-SA, and HeLa carcinoma cell lines was determined. The results revealed that UK-1 and four of these analogues (15-18) are potent against the cancer cell lines. In particular, compound 16 is more potent than UK-1 against A-549 and HeLa cell lines, and compounds 15, 17, and 18 selectively exhibit potent cytotoxic activity against the BFTV-905 cells (IC50 9.6 PM), A-549 cells (IC50 6.6 mu M), and MES-SA cells (IC50 9.2 mu M),respectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.007

文献信息

• Synthesis and Antifungal Activity of Substituted 2‐Aryl Benzimidazoles Derivatives
  作者：Daye Huang、Fang Qiu、Zhigang Zhang、Liqiao Shi、Chunxia Cao、Shaoyong Ke

  DOI：10.1002/jhet.3639

  日期：2019.9

  Benzimidazole fungicides were among the early systemic fungicides developed and used for controlling a wide variety of plant diseases. During the course of our screening process for active compounds, two 2‐aryl benzimidazoles derivatives bearing sulfoxide group (6b and 6c) have been demonstrated to exhibit good inhibition activity against high‐resistant isolate of Botrytis cinerea compared with carbendazim

  苯并咪唑类杀菌剂是早期开发的系统性杀菌剂，可用于控制多种植物病害。在我们筛选活性化合物的过程中，已证明带有亚砜基团的两个2-芳基苯并咪唑衍生物（6b和6c）与多菌灵相比对灰葡萄孢的高抗性分离株表现出良好的抑制活性，抑制率为当浓度为10μg/ mL时，最高可达46.67％和51.11％，这可能被认为是发现新的杀菌剂以分离出高抗性的灰葡萄孢菌的有效框架。
• Water Oxidation by Single-Site Ruthenium Complexes: Using Ligands as Redox and Proton Transfer Mediators
  作者：Markus D. Kärkäs、Torbjörn Åkermark、Eric V. Johnston、Shams R. Karim、Tanja M. Laine、Bao-Lin Lee、Tobias Åkermark、Timofei Privalov、Björn Åkermark

  DOI：10.1002/anie.201205018

  日期：2012.11.12

  Light me up: Through the use of an imidazole motif it is possible to introduce a combined redox and proton‐transfer mediator into single‐site ruthenium water‐oxidation catalysts. With the complex (see picture), high turnover numbers and high initial turnover frequencies were attained with the mild oxidant [Ru(bpy)3]3+ (bpy=2,2′‐bipyridine).

  点亮我：通过使用咪唑基序，可以将氧化还原和质子转移介体结合使用到单中心钌水氧化催化剂中。使用该复合物（参见图片），使用轻度氧化剂[Ru（bpy）3 ] 3+（bpy = 2,2'-联吡啶）可获得高的转换数量和较高的初始转换频率。
• Exploring the importance of zinc binding and steric/hydrophobic factors in novel HCV replication inhibitors
  作者：Daniel C. Talley、Leen Delang、Johan Neyts、Pieter Leyssen、Paul J. Smith

  DOI：10.1016/j.bmcl.2016.01.035

  日期：2016.2

  Several novel compounds have been identified that inhibit the replication of hepatitis C virus in a replicon assay with EC50 values as low as 0.6 mu M. Lead compounds were modified to investigate the possible role that zinc binding may play in inhibitor efficacy. In addition, the structure-activity relationship was explored to increase inhibitor efficacy and possibly identify favorable interactions within the currently unknown inhibitor binding pocket. The rationale for inhibitor design and biological results are presented herein. (C) 2016 Elsevier Ltd. All rights reserved.
• Synthesis and anticancer evaluation of bis(benzimidazoles), bis(benzoxazoles), and benzothiazoles
  作者：Shu-Ting Huang、I-Jen Hsei、Chinpiao Chen

  DOI：10.1016/j.bmc.2006.05.007

  日期：2006.9

  Four classes of UK-1 analogues were synthesized and their cytotoxicity testing against human A-549, BFTC-905, RD, MES-SA, and HeLa carcinoma cell lines was determined. The results revealed that UK-1 and four of these analogues (15-18) are potent against the cancer cell lines. In particular, compound 16 is more potent than UK-1 against A-549 and HeLa cell lines, and compounds 15, 17, and 18 selectively exhibit potent cytotoxic activity against the BFTV-905 cells (IC50 9.6 PM), A-549 cells (IC50 6.6 mu M), and MES-SA cells (IC50 9.2 mu M),respectively. (c) 2006 Elsevier Ltd. All rights reserved.
• Donepezil-based hybrids as multifunctional anti-Alzheimer's disease chelating agents: Effect of positional isomerization
  作者：Marina Costa、Romane Josselin、Diana F. Silva、Sandra M. Cardoso、Nóra V. May、Sílvia Chaves、M. Amélia Santos

  DOI：10.1016/j.jinorgbio.2020.111039

  日期：2020.5

  such as cholinergic dysfunction, deposits of amyloid beta (Aβ) peptide and metal dyshomeostasis. In order to continue the search for new anti-AD drugs, a design strategy was once more followed based on repositioning donepezil (DNP) drug, by ortho-attaching a benzylpiperidine mimetic of DNP moiety to a hydroxyphenyl-benzimidazole (BIM) chelating unit (compound 1). Herein, compound 1 and a positional

  阿尔茨海默氏病（AD）的复杂和多因素性质要求能够击中不同的病理生理的目标，如胆碱能功能障碍，淀粉样蛋白β（A存款化合物的开发β）肽和金属dyshomeostasis。为了继续寻找新的抗AD药物，在重新定位多奈哌齐（DNP）药物的基础上，通过将DNP部分的苄基哌啶模拟物与羟基苯基-苯并咪唑（BIM）螯合单元邻位连接，再次遵循了一种设计策略（化合物1）。在此，化合物1和位置异构体2在它们的潜在的多个性能方面相比：两者都存在良好乙酰胆碱酯酶（AChE）抑制（低微摩尔范围），并且A的中等/良好抑制剂β自和Cu介导的聚集，抑制过程为主要是由于配体之间插原纤维的β-折叠；化合物1对Cu 2+和Zn 2+的螯合能力（pCu = 14.3，pZn = 6.4，pH 7.4，C L / C M  = 10，C M  = 10 -6  M）具有比2（pCu = 10.7， pZn = 6.3），归因于其建立三