2-(5-bromo-1H-benzo[d]imidazol-2-yl)phenol | 1844-41-3

• 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-bromo-1H-benzo[d]imidazol-2-yl)phenol
• 英文别名: 2-(5-bromo-1H-benzimidazol-2-yl)phenol；5-Brom-2-<2-hydroxy-phenyl>-benzimidazol；2-(5-bromo-1(3)H-benzoimidazol-2-yl)-phenol；2-(6-bromo-1H-benzimidazol-2-yl)phenol
• CAS: 1844-41-3
• 化学式: C₁₃H₉BrN₂O
• 分子量: 289.131
• InChiKey: LIOJVPKXLNOWTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 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：

  1,2-二溴乙烷 、 2-(5-bromo-1H-benzo[d]imidazol-2-yl)phenol 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以58%的产率得到11-bromo-6,7-dihydrobenzo[f]benzo[4,5]imidazo[1,2-d][1,4]oxazepine
  参考文献：
  名称：

  6,7-Dihydrobenzo[f]benzo[4,5]imidazo[1,2-d][1,4]oxazepine derivatives as selective inhibitors of PI3Kα

  摘要：

  Twenty eight 6,7-dihydrobenzo[f]benzo[4,5]imidazo[1,2-d][1,4] oxazepine derivatives were synthesized and evaluated their biological activities as PI3K inhibitors. Biological evaluation against four human tumor cell lines revealed that most target compounds showed impressively better antiproliferative activities than that of LY294002. Among these compounds, compound 25 exhibited the most potent and selective activity for PI3K alpha, with the IC50 value of 0.016 mu M, an approximately 30-fold increase in comparison with LY294002, it also has an increased potency of approximately 11-fold for PI3K beta. It indicated the potential of developing 6,7-dihydrobenzo[f] benzo[4,5]imidazo[1,2-d][1,4] oxazepine derivatives as the new PI3K alpha selective inhibitors for tumor treatment. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.01.052
• 作为产物：
  描述：

  水杨醛 、 4-溴邻苯二胺 在 sodium disulfite 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-(5-bromo-1H-benzo[d]imidazol-2-yl)phenol
  参考文献：
  名称：

  6,7-Dihydrobenzo[f]benzo[4,5]imidazo[1,2-d][1,4]oxazepine derivatives as selective inhibitors of PI3Kα

  摘要：

  Twenty eight 6,7-dihydrobenzo[f]benzo[4,5]imidazo[1,2-d][1,4] oxazepine derivatives were synthesized and evaluated their biological activities as PI3K inhibitors. Biological evaluation against four human tumor cell lines revealed that most target compounds showed impressively better antiproliferative activities than that of LY294002. Among these compounds, compound 25 exhibited the most potent and selective activity for PI3K alpha, with the IC50 value of 0.016 mu M, an approximately 30-fold increase in comparison with LY294002, it also has an increased potency of approximately 11-fold for PI3K beta. It indicated the potential of developing 6,7-dihydrobenzo[f] benzo[4,5]imidazo[1,2-d][1,4] oxazepine derivatives as the new PI3K alpha selective inhibitors for tumor treatment. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.01.052

文献信息

• Syntheses, in vitro evaluation and molecular docking studies of 5-bromo-2-aryl benzimidazoles as α-glucosidase inhibitors
  作者：Tanzila Arshad、Khalid Mohammed Khan、Najma Rasool、Uzma Salar、Shafqat Hussain、Tehreem Tahir、Mohammed Ashraf、Abdul Wadood、Muhammad Riaz、Shahnaz Perveen、Muhammad Taha、Nor Hadiani Ismail

  DOI：10.1007/s00044-016-1614-y

  日期：2016.9

  Based on the previous reports on alpha-glucosidase inhibitory activity of benzimidazole class, we intend to evaluate further this class as potential inhibitors of alpha-glucosidase enzyme. Thus, in the current study synthesis of 5-bromo-2-aryl benzimidazole derivatives 1-25 was carried out. All the synthetic compounds were characterized by different spectroscopic techniques EIMS, HRMS, H-1-NMR, and C-13-NMR. Molecular docking was also performed on the selected compounds 1, 4, 7, and 17 having varying substitution pattern in order to understand the molecular interaction of molecules with the active site of the enzyme. All compounds were evaluated for their in vitro alpha-glucosidase inhibitory activities. Twenty-three compounds out of twenty-five showed excellent to moderate activity in the range of IC50 = 12.4-103.2 mu M. Inhibitory results were compared with the standard drug acarbose (IC50 = 38.25 +/- 0.12 mu M). Compounds 1 (IC50 = 37.82 +/- 0.08 mu M), 9 (IC50 = 37.76 +/- 0.05 mu M), 12 (IC50 = 24.96 +/- 0.09 mu M), 16 (IC50 = 21.15 +/- 0.08 mu M) and 17 (IC50 = 8.34 +/- 0.02 mu M) showed excellent inhibition as compared to standard drug acarbose (IC50 = 38.25 +/- 0.12 mu M). Especially, 17 (IC50 = 8.34 +/- 0.02 mu M) was found to be five-fold more active than the standard.
• Spectral characterization, antibacterial and antioxidant activity of 2-(5-bromo-1H-benzimidazol-2-yl)-(3’/4’/5’-substituted)phenols and some transition metal complexes
  作者：Aydin TAVMAN、Demet GÜRBÜZ、Ayça Aktaş KARAÇELİK、Dilşat Nigar ÇOLAK、Derya EFE、Adem ÇINARLI

  DOI：10.33224/rrch.2024.69.3-4.10

  日期：2024.3.15

  2-(5-Bromo-1H-benzimidazol-2-yl)-3'/4'/5'-substituted-phenols (HL1 – HL25) were synthesized and characterized using various spectroscopic techniques. Then, Fe(III), Co(II), Ni(II), Cu(II), Zn(II), Ru(III) complexes of 2-(5-bromo-1H-benzimidazol-2-yl)phenol (HL1) were prepared and the methods such as elemental analysis, thermogravimetric analysis (TGA), molar conductivity and magnetic moment measurements, FT-IR, fluorescence and NMR spectroscopy were used to make suggestions about structures of the complexes. It is interesting that the compounds HL12 and HL22 showed stronger fluorescence effects than the others. The common feature of these two compounds is that they have a fluorine substituent at the 4'-position on the phenol ring. In addition, antioxidant and antibacterial activity of the compounds were investigated. The first three compounds showing the best antioxidant activity are HL25 (trihydroxy derivative: 4-(5-bromo-1H-benzimidazol-2-yl)benzene-1,2,3-triol), HL8 (2,5-dihydroxy derivative) and HL6 (2,3-dihydroxy derivative). It was observed that HL25 showed higher antioxidant activity than the reference substances 3,5-di-tert-4-butylhydroxytoluene (BHT) and Trolox both in terms of 1,1-diphenyl-2-picrylhydrazyl radical (DPPH•) scavenging (0.0018 mg/mL) and ferric reducing / antioxidant power (FRAP) methods trolox equivalent antioxidant capacity (TEAC) value: 1564.44±1.92}. The second and third hydroxy groups added to HL1 appear to significantly increase the antioxidant activity. It was determined that complexes of HL1 showed much better antioxidant effect with respect to HL1. The derivatives with the highest antibacterial effect were found to be HL14 (nitro derivative), HL8, HL6 and HL25 having moderate activity. The high levels of both antioxidant and antibacterial activities of HL6, HL8 and HL25 indicate a correlation between their antibacterial and antioxidant effects. It was observed that the Ru(III) and Co(II) complexes showed moderate antibacterial activity whereas the ligand was inactive.