2-(4-甲氧基苯基)-1H-苯并咪唑-5-羧酸 | 174422-17-4

• 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-(4-甲氧基苯基)-1H-苯并咪唑-5-羧酸
• 中文别名: 环己乙酸,4-[4-(4-氨基-7,7-二甲基-7H-嘧啶并[4,5-b][1,4]噁嗪-6-基)苯基]-,反-
• 英文名称: 2-(4-methoxyphenyl)-1H-benzo[d]imidazole-5-carboxylic acid
• 英文别名: 2-(4-methoxyphenyl)-3H-benzimidazole-5-carboxylic acid
• CAS: 174422-17-4
• 化学式: C₁₅H₁₂N₂O₃
• 分子量: 268.272
• InChiKey: VQGVZGRTDWXQJE-UHFFFAOYSA-N

物化性质

• 熔点：
  118 °C
• 沸点：
  550.9±56.0 °C(Predicted)
• 密度：
  1.362±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  75.2
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi

反应信息

• 作为反应物：
  描述：

  2-(4-甲氧基苯基)-1H-苯并咪唑-5-羧酸 在 甲醇 、 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 4''-O-(2-(4-methoxyphenyl)-1H-benzimidazole-5-carbonyl)hydrazinecarbonylclarithromycin
  参考文献：
  名称：

  Synthesis and antibacterial activity of novel 4″-O-benzimidazolyl clarithromycin derivatives

  摘要：

  Novel 4 ''-O-benzimidazolyl clarithromycin derivatives were designed, synthesized and evaluated for their in vitro antibacterial activities. These benzimidazolyl derivatives exhibited excellent activity against erythromycin-susceptible strains better than the references, and some of them showed greatly improved activity against erythromycin-resistant strains. Compounds 16 and 17, which have the terminal 2-(4-methylphenyl)benzimidazolyl and 2-(2-methoxyphenyl)benzimidazolyl groups on the C-4 '' bishydrazide side chains, were the most active against erythromycin-resistant Staphylococcus pneumoniae expressing the erm gene and the me! gene. In addition, compound 17 exhibited the highest activity against erythromycin-susceptible S. pneumoniae ATCC49619 and Staphylococcus aureus ATCC25923 as well. It is worth noting that the 4 ''-O-(2-aryl)benzimidazolyl derivatives show higher activity against erythromycin-susceptible and erythromycin-resistant strains than the 4 ''-O-(2-alkyl) benzimidazolyl derivatives. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.04.004
• 作为产物：
  描述：

  methyl 2-(4-methoxyphenyl)-1H-benzo[d]imidazole-5-carboxylate 在 盐酸 、 溶剂黄146 作用下， 反应 3.0h， 生成 2-(4-甲氧基苯基)-1H-苯并咪唑-5-羧酸
  参考文献：
  名称：

  针对BRCA1 tBRCT域的蛋白质与蛋白质相互作用的小分子抑制剂的结构指导合成和评价。

  摘要：

  BRCA1的串联BRCT结构域（tBRCT）结合靶蛋白中的含磷酸丝氨酸的基序，以传播由DNA损伤引发的细胞内信号，从而控制细胞周期停滞和DNA修复。最近，我们确定了Bractoppin，BRCA1 tBRCT域的第一个小分子抑制剂，该抑制剂选择性地中断DNA损伤引起的BRCA1介导的细胞反应。在这里，我们结合结构指导的化学精制，蛋白质诱变和细胞分析来定义负责Bractoppin活性的结构特征。Bractoppin无法结合BRCA1 tBRCT的突变形式，该突变形式带有K1702A，介导磷酸肽识别的关键残基，或邻接pSer识别位点的F1662R或L1701K。但是，M1775R突变与共有磷酸肽基序pSer-XX-Phe中的Phe残基结合，不会影响Bractoppin的结合，从而证实了与底物磷酸肽结合不同的结合方式。我们在生化分析中通过结构指导的化学加工和表征的构效关系（SAR）探索了这些结构

  DOI：

  10.1002/cmdc.201900300

文献信息

• Novel Clarithromycin Analogs with C-4” 2-arylbenzimidazolyl Bishydrazide Side Chain: Synthesis and Antibacterial Evaluation
  作者：Yunkun Qi、Ruixin Ma、Xin Li、Yue Hu、Siti Ma、Chao Cong、Xiaodong Ma、Wenping Cui、Shutao Ma

  DOI：10.2174/157018011797655269

  日期：2011.12.1

  A series of novel 4” -O-2-arylbenzimidazolyl derivatives of clarithromycin were synthesized and evaluated. These 4” -O-2-arylbenzimidazolyl derivatives demonstrated excellent activity against erythromycin-susceptible strains and showed remarkably improved activity against erythromycin-resistant strains compared with the references. In particular, compound 7c, which possesses the terminal 2-(2-methoxyphenyl)benzimidazolyl group on the C-4” bishydrazide side chain, not only presented the most potent activity against erythromycin-susceptible Streptococcus pneumoniae ATCC49619 and Staphylococcus aureus ATCC25923, exhibiting 4-fold and 4-fold higher efficacy than the parent clarithromycin, but also displayed the highest activity against erythromycin-resistant Streptococcus pneumoniae expressing the mef gene and the erm gene, which was 133-fold and 32-fold better than clarithromycin or azithromycin, respectively.

  一系列新型的克拉霉素4”-O-2-芳基苯并咪唑衍生物被合成并评估。这些4”-O-2-芳基苯并咪唑衍生物对红霉素敏感菌株显示出优异的活性，并且相较于参考药物，对红霉素耐药菌株的活性显著提高。特别是化合物7c，其在C-4”双酰肼侧链上带有末端的2-（2-甲氧基苯基）苯并咪唑基团，不仅对红霉素敏感的肺炎链球菌ATCC49619和金黄色葡萄球菌ATCC25923表现出最强的活性，效能分别是母体克拉霉素的4倍和4倍，而且对表达mef基因和erm基因的红霉素耐药肺炎链球菌的活性也是最高的，分别是克拉霉素或阿奇霉素的133倍和32倍。
• NOVEL COMPOUND HAVING SKIN-WHITENING, ANTI-OXIDIZING AND PPAR ACTIVITIES AND MEDICAL USE THEREFOR
  申请人：Chung Hae Young

  公开号：US20140037564A1

  公开（公告）日：2014-02-06

  Provided are a novel compound having skin-whitening, anti-oxidizing and PPAR activities and a medical use thereof, and the compound has skin-whitening activities for the suppression of tyrosinase, and accordingly, is useful for use in skin-whitening pharmaceutical composition or cosmetic products; has anti-oxidant activities, and accordingly, is useful for the prevention and treatment of skin-aging; and has PPAR activities, and in particular, PPARα and PPARγ activities, and accordingly, is useful for use in pharmaceutical compositions or health foods which are effective for the prevention and treatment of obesity, metabolic disease, or cardiovascular disease.

  提供了一种具有美白皮肤、抗氧化和PPAR活性的新化合物及其医药用途，该化合物具有抑制酪氨酸酶的美白皮肤活性，因此适用于用于美白皮肤的药用组合物或化妆品；具有抗氧化活性，因此适用于预防和治疗皮肤衰老；具有PPAR活性，特别是PPARα和PPARγ活性，因此适用于用于预防和治疗肥胖、代谢性疾病或心血管疾病的药用组合物或保健食品。
• [EN] HEMATOPOIETIC GROWTH FACTOR MIMETIC SMALL MOLECULE COMPOUNDS AND THEIR USES<br/>[FR] COMPOSÉS À PETITES MOLÉCULES MIMÉTIQUES DES FACTEURS DE CROISSANCE HÉMATOPOÏÉTIQUE ET LEURS UTILISATIONS
  申请人：LIGAND PHARM INC

  公开号：WO2011046954A1

  公开（公告）日：2011-04-21

  The present embodiments relate to compounds with physiological effects, such as the activation of hematopoietic growth factor receptors. The present embodiments also relate to use of the compounds to treat a variety of conditions, diseases and ailments such as hematopoietic conditions and disorders.

  目前的实施例涉及具有生理效应的化合物，例如激活造血生长因子受体。目前的实施例还涉及利用这些化合物来治疗各种疾病、疾病和疾患，如造血状况和疾病。
• Synthesis and antimicrobial activity of some new benzimidazole carboxylates and carboxamides
  作者：Gülgün Ayhan-Kılcıgil、Meral Tunçbilek、Nurten Altanlar、Hakan Göker

  DOI：10.1016/s0014-827x(99)00059-2

  日期：1999.8

  Some benzimidazole carboxylates and carboxamides were synthesized and evaluated for their antimicrobial activities against Staphylococcus aureus, Escherichia coli and Candida albicans. Among the investigated compounds 2d exhibited best activity against C. albicans.

  合成了一些苯并咪唑羧酸盐和羧酰胺，并评估了它们对金黄色葡萄球菌，大肠杆菌和白色念珠菌的抗菌活性。在所研究的化合物中，2d表现出对白色念珠菌的最佳活性。
• Synthesis of Glycal-Based Chiral Benzimidazoles by VO(acac)₂−CeCl₃ Combo Catalyst and Their Self-Aggregated Nanostructured Materials
  作者：Dilip K. Maiti、Samiran Halder、Palash Pandit、Nirbhik Chatterjee、Dripta De Joarder、Nabyendu Pramanik、Yasmin Saima、Amarendra Patra、Prabir K. Maiti

  DOI：10.1021/jo901458k

  日期：2009.11.6

  combo catalyst has been developed for chemoselective cyclocondensation cum oxidation under mild reaction conditions toward synthesis of a new class of optically pure compounds, 2-(2′-C-3′,4′,6′-tri-O-benzyl/methyl-glycal)-1H-benzimidazoles. It involves an operationally simple synthetic protocol efficient for the syntheses of a wide range of chiral benzimidazoles in high yields without formation of undesired

  已开发出VO（acac）2 -CeCl 3组合催化剂，用于在温和的反应条件下进行化学选择性环缩合和氧化，以合成新型光学纯化合物2-（2'- C -3'，4'，6'-三-O-苄基/甲基-糖基）-1 H-苯并咪唑。它涉及一种操作简单的合成方案，可有效地高产率地合成多种手性苯并咪唑，而不会形成不希望的1,2-二取代和假糖副产物。钒（V）被发现是化学过程中的活性氧化剂，通过紫外吸收光谱法对其进行了研究。高阶一维低分子量有机纳米结构材料是通过手性纳米级结构单元的纳米结晶而制备的。糖基手性苯并咪唑的B3LYP / 6-31G **理论水平的理论计算显示出1 H-蒽的平面几何形状[1,2- d]咪唑-6,11-二酮部分，负责强烈的自聚集，生成超长纳米结构材料。我们还发现理论结果与2D-NOESY实验中的实验观察结果之间有很好的一致性。还报道了固体纳米结构材料的光物理性质。