2-(4-hydroxyphenyl)-3H-benzoimidazole-5-carbaldehyde | 129012-05-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-(4-hydroxyphenyl)-3H-benzoimidazole-5-carbaldehyde
• 英文别名: 5-formyl-2-(4-hydroxyphenyl)-3H-benzimidazole；2-(4-hydroxyphenyl)-3H-benzimidazole-5-carbaldehyde
• CAS: 129012-05-1
• 化学式: C₁₄H₁₀N₂O₂
• 分子量: 238.246
• InChiKey: FDOHGBWCYJDUFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 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：
  66
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-hydroxyphenyl)-3H-benzoimidazole-5-carbaldehyde 在 sodium hydroxide 、 sodium disulfite 作用下， 以 乙醇 、 水 为溶剂， 反应 20.5h， 生成 2'-(4-hydroxyphenyl)-6-(4-methylpiperazin-1-yl)-1H,3'H-2,5'-bibenzoimidazoyl-4-carboxylic acid
  参考文献：
  名称：

  Design of New Bidentate Ligands Constructed of Two Hoechst 33258 Units for Discrimination of the Length of Two A₃T₃ Binding Motifs

  摘要：

  The aim of this study is to develop bidentate minor-groove binders that bind the double binding motifs cooperatively. The new bidentate ligands (1) have been designed by connecting two Hoechst 33258 units with a polyether linker for cooperative binding with two remote A(3)T(3) sites of DNA. The linker is introduced to the benzimidazole ring so that it is located at the convex side of the Hoechst unit. DNA binding affinity of the ligands was evaluated by measuring surface plasmon resonance (SPR), circular dichroism, and fluorescence spectra. Interestingly, the bidentate ligands (1) did not show affinity to DNA1 with a single A(3)T(3) motif but showed selective affinity to DNA2 with two A(3)T(3) motifs. The Long Bis-H (1L) having a long polyether linker showed specific binding to DNA2(6) with two A3T3 motifs separated by six nonbinding base pairs. The Long Bis-H (1L) has also shown specific binding to the three-way junction DNA4 with two A(3)T(3) motifs. This study has demonstrated that DNA with double binding motifs can be selectively recognized by the newly designed bidentate ligands.

  DOI：

  10.1021/jo051836t
• 作为产物：
  描述：

  3,4-二氨基苯甲腈 在 sodium metabisulfite 、 甲酸 、 nickel aluminum 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 生成 2-(4-hydroxyphenyl)-3H-benzoimidazole-5-carbaldehyde
  参考文献：
  名称：

  新型双苯并咪唑类化合物作为大肠杆菌拓扑异构酶IA抑制剂和潜在抗菌剂的合成及生物学评价

  摘要：

  新型细菌IA型拓扑异构酶的双苯并咪唑抑制剂对于开发受靶标介导的氟喹诺酮类交叉抗药性影响的新型抗菌剂具有重要意义。本研究证明了比苯并咪唑类似物作为大肠杆菌拓扑异构酶IA抑制剂的成功合成和评估。5-（4-丙基哌嗪-1-基）-2- [2'-（4-乙氧基苯基）-5'-苯并咪唑基]苯并咪唑（12b）对EcTopo 1A表现出明显的松弛抑制活性（IC 50 = 2± 0.005μM ）和螯合金属离子的趋势。有趣的是，这些化合物对大肠杆菌DNA促旋酶和hTop 1的抑制作用均不超过100μM。化合物12b在评估的24种化合物中，对大肠杆菌菌株的MIC最低。从等温滴定量热法（ITC）观察到12b与EcTopo 1A的结合亲和常数和结合自由能分别为6.8×10 6 M –1和-10.84 kcal mol –1。体内小鼠全身感染和中性粒细胞减少大腿模型的实验结果证实了12b的治疗功效，表明这类化合物作为抗菌剂的进一步发展。

  DOI：

  10.1021/jm5003028

文献信息

• Synthesis and investigation of novel benzimidazole derivatives as antifungal agents
  作者：Nishad Thamban Chandrika、Sanjib K. Shrestha、Huy X. Ngo、Sylvie Garneau-Tsodikova

  DOI：10.1016/j.bmc.2016.06.010

  日期：2016.8

  pathogenic fungal strains have resulted in an increase in demand for new antifungal agents. Various heterocyclic scaffolds with different mechanisms of action against fungi have been investigated in the past. Herein, we report the synthesis and antifungal activities of 18 alkylated mono-, bis-, and trisbenzimidazole derivatives, their toxicities against mammalian cells, as well as their ability to induce

  多种病原性真菌菌株对抗真菌药物的抵抗性的上升和出现导致对新抗真菌药物的需求增加。过去已经研究了具有不同作用机理的多种杂环支架。本文中，我们报道了18种烷基化的单，双和三苯并咪唑衍生物的合成和抗真菌活性，它们对哺乳动物细胞的毒性以及在酵母细胞中诱导活性氧（ROS）的能力。我们的许多双苯并咪唑化合物对所有测试的真菌菌株均表现出中等至出色的抗真菌活性，MIC值为15.6至0.975μg/ mL。发现我们的双苯并咪唑类的真菌活性谱取决于烷基链长。
• Bi-functional complexes and methods for making and using such complexes
  申请人：Gouliaev Alex Haahr

  公开号：US11225655B2

  公开（公告）日：2022-01-18

  The present invention is directed to a method for the synthesis of a bi-functional complex comprising a molecule part and an identifier oligonucleotide part identifying the molecule part. A part of the synthesis method according to the present invention is preferably conducted in one or more organic solvents when a nascent bi-functional complex comprising an optionally protected tag or oligonucleotide identifier is linked to a solid support, and another part of the synthesis method is preferably conducted under conditions suitable for enzymatic addition of an oligonucleotide tag to a nascent bi-functional complex in solution.

  本发明涉及一种合成双功能复合物的方法，该复合物包括分子部分和识别分子部分的识别寡核苷酸部分。根据本发明的合成方法的一部分优选在一种或多种有机溶剂中进行，此时包含可选保护标签或寡核苷酸标识符的新生双功能复合物与固体支持物相连接，合成方法的另一部分优选在适合于将寡核苷酸标签酶加到溶液中的新生双功能复合物的条件下进行。
• Yadagiri, Bathini; Lown, J. William, Synthetic Communications, 1990, vol. 20, # 7, p. 955 - 963
  作者：Yadagiri, Bathini、Lown, J. William

  DOI：——

  日期：——
• BI-FUNCTIONAL COMPLEXES AND METHODS FOR MAKING AND USING SUCH COMPLEXES
  申请人：Nuevolution A/S

  公开号：EP2558577A1

  公开（公告）日：2013-02-20
• METHODS AND COMPOSITIONS RELATED TO VIRAL INHIBITION
  申请人：Arya Dev P.

  公开号：US20110046982A1

  公开（公告）日：2011-02-24

  Disclosed herein are compounds, compositions and methods related to viral inhibition. In some forms, the compounds, compositions and methods are related to binding RNA.