2-(5-chloro-1H-benzimidazol-2-yl)-4-bromophenol | 1096958-87-0

• 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-benzimidazol-2-yl)-4-bromophenol
• 英文别名: 4-bromo-2-(6-chloro-1H-benzimidazol-2-yl)phenol
• CAS: 1096958-87-0
• 化学式: C₁₃H₈BrClN₂O
• mdl: MFCD11539899
• 分子量: 323.576
• InChiKey: BUAYQHRTMASAOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 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：

  2-(5-chloro-1H-benzimidazol-2-yl)-4-bromophenol 、 1,2-二溴乙烷 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以71%的产率得到2-bromo-11-chloro-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：

  4-氯-1,2-苯二胺 、 5-溴水杨醛 在 sodium hydrogensulfite 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以64%的产率得到2-(5-chloro-1H-benzimidazol-2-yl)-4-bromophenol
  参考文献：
  名称：

  Tavman, Aydin; Ikiz, Serkan; Bagcigil, A. Funda, Bulletin of the Chemical Society of Ethiopia, 2010, vol. 24, # 3, p. 391 - 400

  摘要：

  DOI：

文献信息

• Spectral characterization and antimicrobial activity of Cu(II) and Fe(III) complexes of 2-(5-Cl/NO₂-1<i>H</i>-benzimidazol-2-yl)-4-Br/NO₂-phenols
  作者：Aydin Tavman、Ismail Boz、A. Seher Birteksöz、Adem Cinarli

  DOI：10.1080/00958971003789835

  日期：2010.4.20

  The compounds of 2-(5-chloro/nitro-1H-benzimidazol-2-yl)-4-bromo/nitrophenols (HLX : X = 1-4) and their copper(II) nitrate and iron(III) nitrate complexes have been synthesized and characterized. The structures of the complexes were confirmed on the basis of elemental analysis, thermal gravimetric analysis, molar conductivity and magnetic moment measurements, FT-IR, mass, and UV-Vis spectroscopy techniques. The complexes show high-thermal stability with 350 degrees C m.p. In all complexes, the ligands are bidentate via one imine nitrogen and a phenolate oxygen. Cu(II) complexes having 1 : 2 M : L ratio are classified as non-electrolytes, whereas 1 : 1 M : L ratio is observed in Fe(III) complexes except [Fe(L3)2(H2O)2](NO3) 3H2O. The antimicrobial activities of the ligands and the complexes were evaluated using the disc diffusion method in DMSO as well as minimum inhibitory concentration dilution method against Staphylococcus aureus, Staphylococcus epidermidis, Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, and Proteus mirabilis. Antifungal activities were reported for Candida albicans. The complexes [Fe(L3)2(H2O)2](NO3) 3H2O and [Cu(L3)2] 2H2O are more effective against S. epidermidis than ciprofloxacin.
• Spectral characterization and antimicrobial activity of 2-(5-chloro/nitro-1H-benzimidazol-2-yl)-4-bromo/nitro-phenols and their zinc(II) complexes
  作者：Aydin Tavman、Ismail Boz、A. Seher Birteksöz

  DOI：10.1016/j.saa.2010.05.008

  日期：2010.9

  2-(5-Chloro/nitro-1H-benzimidazol-2-yl)-4-bromo/nitro-phenols (HL(x); x=1-4) and their complexes with zinc(II)nitrate have been synthesized and characterized. In the tetrahedral mononuclear complexes, the ligands are bidentate, via the imine nitrogen and the phenolate oxygen atoms. The structures of the complexes were confirmed on the basis of elemental analysis, molar conductivity, TGA, FT-IR. NMR, mass and UV-vis spectroscopy. The optimized geometry of the complexes was derived from theoretical calculation in DGauss/DFT level on CACHE program. From theoretical calculations it was found that bromo derivatives of the ligands (HL(1) and HL(3)) have higher stability than the other ligands and similarly, their Zn(II) complexes have higher stability than the other complexes. The antimicrobial activities of the compounds were evaluated using the disk diffusion method against six bacteria and Candida albicans. All of the complexes exhibited selective antibacterial activity on Staphylococcus epidermidis. HL(3) and [Zn(L(1))(2)]center dot H(2)O are more active than Ciprofloxazin and, [Zn(L(2))(2)] has antibacterial activity as potent as Ciprofloxazin against S. epidermidis. (c) 2010 Elsevier B.V. All rights reserved.