2-(5-chloro-1H-benzo[d]imidazol-2-yl)phenol | 14313-44-1

• 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-(5-chloro-1H-benzo[d]imidazol-2-yl)phenol
• 英文别名: 2-(5-Chloro-1h-benzimidazole-2-yl)phenol；2-(6-chloro-1H-benzimidazol-2-yl)phenol
• CAS: 14313-44-1
• 化学式: C₁₃H₉ClN₂O
• mdl: MFCD11103114
• 分子量: 244.68
• InChiKey: MFBAVZSGFJYZLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  48.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  壬酸 、 2-(5-chloro-1H-benzo[d]imidazol-2-yl)phenol 在 PPA 作用下， 反应 6.0h， 以13%的产率得到1-[3-(5-Chloro-1H-benzoimidazol-2-yl)-4-hydroxy-phenyl]-nonan-1-one
  参考文献：
  名称：

  Substituted 2-(2-hydroxyphenyl)benzimidazoles as potential agents for the control of periodontal diseases

  摘要：

  A series of 16 substituted 2-(2-hydroxphenyl)benzimidazoles was synthesized and evaluated in vitro for antibacterial activity against bacteria associated with periodontal diseases. Several compounds demonstrated a high level of activity, in tube dilution assay, against Actinomycetes viscosus and Bacteriodes gingivalis. These results indicate that several of these compounds may serve as topical antibacterial agents for the control of acute marginal inflammatory gingivitis and periodontitis.

  DOI：

  10.1021/jm00384a035
• 作为产物：
  描述：

  水杨酰胺 在 四氢吡咯 、 三氯氧磷 、 三氯化磷 作用下， 以 乙腈 、 苯 为溶剂， 反应 23.0h， 生成 2-(5-chloro-1H-benzo[d]imidazol-2-yl)phenol
  参考文献：
  名称：

  Substituted 2-(2-hydroxyphenyl)benzimidazoles as potential agents for the control of periodontal diseases

  摘要：

  A series of 16 substituted 2-(2-hydroxphenyl)benzimidazoles was synthesized and evaluated in vitro for antibacterial activity against bacteria associated with periodontal diseases. Several compounds demonstrated a high level of activity, in tube dilution assay, against Actinomycetes viscosus and Bacteriodes gingivalis. These results indicate that several of these compounds may serve as topical antibacterial agents for the control of acute marginal inflammatory gingivitis and periodontitis.

  DOI：

  10.1021/jm00384a035

文献信息

• Synthesis and biological activity evaluation of 1H-benzimidazoles via mammalian DNA topoisomerase I and cytostaticity assays
  作者：Gunes Coban、Sevil Zencir、István Zupkó、Borbála Réthy、H. Semih Gunes、Zeki Topcu

  DOI：10.1016/j.ejmech.2008.06.018

  日期：2009.5

  the reactions of DNA topoisomerases, enzymes functioning at almost all stages of the cell cycle. In this study, nine 1H-benzimidazole derivatives with substituents at positions 2 and 5 were synthesized and the structure of the compounds was elucidated by instrumental methods. The characterized compounds were screened to identify if they interfered with mammalian type I DNA topoisomerase activity via in

  苯并咪唑是重要的化合物，因为它们具有抗菌，抗真菌，抗微生物，抗原生动物和抗蠕虫的活性。一些苯并咪唑衍生物还干扰DNA拓扑异构酶的反应，DNA拓扑异构酶在细胞周期的几乎所有阶段均起作用。在本研究中，九个1 H合成了在2和5位具有取代基的-苯并咪唑衍生物，并通过仪器方法阐明了化合物的结构。通过体外超螺旋弛豫测定法筛选表征的化合物，以鉴定它们是否干扰了哺乳动物的I型DNA拓扑异构酶活性。使用HeLa（宫颈腺癌），MCF7（乳腺腺癌）和A431（皮肤表皮样癌）细胞对所选化合物进行细胞抑制分析。我们的结果表明5-氯-2-（2-羟苯基）-1 H-苯并咪唑发挥了最深刻的拓扑异构酶I抑制和细胞毒性作用。
• 1H-benzimidazole derivatives as butyrylcholinesterase inhibitors: synthesis and molecular modeling studies
  作者：Gunes Coban、Luca Carlino、Ayse Hande Tarikogullari、Sülünay Parlar、Görkem Sarıkaya、Vildan Alptüzün、Ayşe Selcen Alpan、Hasan Semih Güneş、Erçin Erciyas

  DOI：10.1007/s00044-016-1648-1

  日期：2016.9

  A series of N-2-[2-(1H-benzimidazole-2-yl)phenoxy]ethyl} substituted amine derivatives were synthesized and tested for their cholinesterase inhibitor activity. Acetylcholinesterase and butyrylcholinesterase inhibitor activities were evaluated in vitro by using Ellman’s method. According to the activity results, all of the compounds displayed moderate acetylcholinesterase inhibitory activity and most

  合成了一系列的N- 2- [2-（1 H-苯并咪唑-2-基）苯氧基]乙基}取代的胺衍生物，并测试了它们的胆碱酯酶抑制剂活性。使用Ellman方法在体外评估乙酰胆碱酯酶和丁酰胆碱酯酶抑制剂的活性。根据活性结果，所有化合物均表现出中等的乙酰胆碱酯酶抑制活性，大多数化合物表现出显着的丁酰胆碱酯酶抑制活性。化合物3d是该系列中活性最高的化合物，也是选择性的丁酰胆碱酯酶抑制剂。还进行了分子对接研究和分子动力学模拟。
• Ester derivatives of dimethylpropionic acid and pharmaceutical compositions containing them
  申请人：CERMOL S.A.

  公开号：EP1132381A1

  公开（公告）日：2001-09-12

  The present invention relates to esters of 2,2-dimethylpropionic acid having the general formula (I) or pharmacological acceptable salts thereof, as well as to pharmaceutical compositions containing said compounds and having an inhibitory activity of elastase.

  本发明涉及具有通式（I）的2,2-二甲基丙酸酯或其药理学上可接受的盐，以及含有该化合物并具有弹性蛋白酶抑制活性的药物组合物。
• Preparation, characterization, DFT calculations and ethylene oligomerization studies of iron(II) complexes bearing 2-(1H-benzimidazol-2-yl)-phenol derivatives
  作者：Marzieh Haghverdi、Azadeh Tadjarodi、Naeimeh Bahri-Laleh、Mehdi Nekoomanesh Haghighi

  DOI：10.1080/00958972.2018.1446527

  日期：2018.4.18

  Abstract Five 2-(1H-benzimidazol-2-yl)-phenol derivatives including 1H (HL1), 5-chloro-(HL2), 5-methyl-(HL3), 5,6-dichloro-(HL4), and 5,6-dimethyl-(HL5) were synthesized by the reaction of their corresponding benzene-1,2-diamine precursors and 2-hydroxybenzaldehyde which subsequently was employed in complexation with Fe(II) to prepare complexes C1–C5, respectively. Indeed, in all complexes, the ligands

  摘要 五种 2-(1H-苯并咪唑-2-基)-苯酚衍生物，包括 1H (HL1)、5-氯-(HL2)、5-甲基-(HL3)、5,6-二氯-(HL4) 和 5 ,6-二甲基-(HL5) 是通过其相应的苯-1,2-二胺前体和 2-羟基苯甲醛反应合成的，随后将其与 Fe(II) 络合以分别制备配合物 C1-C5。实际上，在所有配合物中，配体分别通过苯并咪唑部分和苯酚环的 C=N 氮和羟基氧原子配位为双齿。通过 FTIR、UV-vis、1H-和 13C-NMR 光谱、ICP 和元素分析（C、H 和 N）对化合物进行表征。这些化合物的纯度由熔点 (mp) 和 TLC 确定。合成的配体和配合物通过 Gaussian09 软件在 B3LYP/TZVP 理论水平进行几何优化，并在分析化合物的 IR 数据时实现了令人满意的理论-实验一致性。针对乙烯反应性研究了铁 (II) 配合物的催化行为。在用二乙基氯化铝 (Et2AlCl)
• Synthesis and insight into the structure–activity relationships of 2-phenylbenzimidazoles as prospective anticancer agents
  作者：Thi-Kim-Chi Huynh、Thi-Hong-An Nguyen、Thi-Cam-Thu Nguyen、Thi-Kim-Dung Hoang

  DOI：10.1039/d0ra02282a

  日期：——

  In order to explore and develop new anticancer agents, three series of 2-phenylbenzimidazoles, 15–46, were condensed under simple and mild conditions using sodium metabisulfite as an oxidation agent and another series, 47–55, were obtained via a reduction reaction using sodium borohydride. All the compounds synthesized were evaluated for their in vitro anticancer activities against three human cancer

  为了探索和开发新型抗癌药物，利用焦亚硫酸钠作为氧化剂，在简单温和的条件下缩合了三个系列的2-苯基苯并咪唑15-46 ，并通过使用还原剂进行还原反应得到了另一个系列47-55 。硼氢化钠。评估了所有合成的化合物对三种人类癌细胞系的体外抗癌活性。新型化合物38被发现是针对A549、MDA-MB-231和PC3细胞系最有效的多癌症抑制剂（IC 50值分别为4.47、4.68和5.50 μg mL -1 ）。此外，化合物40对MDA-MB-231细胞系表现出最佳IC 50值，为3.55 μg mL -1 。结果表明，向化合物37-55引入新的取代基可以提高其抗增殖活性。