2-(5-nitro-1H-benzimidazol-2-yl)-4-bromophenol | 1234382-39-8

• 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-nitro-1H-benzimidazol-2-yl)-4-bromophenol
• 英文别名: 4-bromo-2-(5-nitro-1H-benzoimidazol-2-yl)phenol；4-bromo-2-(6-nitro-1H-benzimidazol-2-yl)phenol
• CAS: 1234382-39-8
• 化学式: C₁₃H₈BrN₃O₃
• 分子量: 334.129
• InChiKey: JXCFLQLOLPKFAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 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：
  94.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(5-nitro-1H-benzimidazol-2-yl)-4-bromophenol 在 potassium phosphate 、 trans-1,2-Diaminocyclohexane 、 铜 、 sodium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 64.0h， 生成 1-(1-(4-hydroxy-3-(6-nitro-1H-benzoimidazol-2-yl)phenyl)-1H-indol-3-yl)-3-(1H-indol-3-yl)prop-2-en-1-one
  参考文献：
  名称：

  苯并咪唑-吲哚-查尔酮连接的甲基丙烯酸酯侧链D-π-A聚合物及其在有机光伏中的应用

  摘要：

  在此，我们报告了四种带有悬垂发色团供体的无金属有机聚甲基丙烯酸甲酯（In-In-BzI）PMA，（Ac-In-BzI）PMA，（TPA-In-BzI）PMA和（Py-In-BzI）PMA。 -π-共轭受体（D-π-A）分子框架作为染料敏化太阳能电池（DSSC）的光敏剂。其中供体-受体单元通过吲哚-查尔酮延伸侧链连接，以抑制反向电子转移和电荷重组；π连接剂组分包含各种基于查尔酮的取代基，以增强太阳能设备的日光收集能力。基于DSSC格式的光子电流电池是使用聚合物作为敏化剂制造的。使用（TPA-In-BzI）PMA组装的DSSC设备在AM 1.5G（100 mW cm –2）的光照下，其IPCE峰值和J – V响应具有显着更好的总体功率转换效率，为3.70％。©2017 Wiley Periodicals，Inc. J. Polym。科学，A部分：Polym。化学 2017年，55，997-1007

  DOI：

  10.1002/pola.28460
• 作为产物：
  描述：

  4-硝基邻苯二胺 、 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 5.0h， 以61%的产率得到2-(5-nitro-1H-benzimidazol-2-yl)-4-bromophenol
  参考文献：
  名称：

  2-（5-硝基-1H-苯并咪唑-2-基）-4-溴苯酚的某些过渡金属配合物的光谱表征和抗菌活性

  摘要：

  摘要 。2-（5-硝基-1 H-苯并咪唑-2-）的MnCl 2，FeCl 3，Ru（DMSO）4 Cl 2，CoCl 2，NiCl 2，PdCl 2，CuCl 2，AgNO 3，CdCl 2和HgCl 2络合物yl）-4-溴苯酚（HL）的合成和表征。根据元素分析，TGA，摩尔电导率和磁矩测量，FT-IR，远红外，FT-拉曼，紫外-可见，NMR和荧光光谱确定复合物的结构。根据分析和光谱数据，该配体通过亚胺氮和酚盐的氧原子起到除Ag（I）以外的金属离子的二齿形式。筛选的复合物对金黄色葡萄球菌，表皮葡萄球菌，大肠杆菌，肺炎克雷伯菌，铜绿假单胞菌，奇异毕赤酵母的体外抗菌活性和对白色念珠菌的抗菌活性。环丙沙星和氟康唑分别用作复合物的抗菌和抗真菌活性的参考。在大多数情况下，测试的复合物对金黄色葡萄球菌表现出相当大的活​​性，尤其是革兰氏阳性细菌。此外，还发现Hg（II）和Ag（I）配合物对所有微生物均

  DOI：

  10.4314/bcse.v33i3.6

文献信息

• 6,7-Dihydrobenzo[f]benzo[4,5]imidazo[1,2-d][1,4]oxazepine derivatives as selective inhibitors of PI3Kα
  作者：Yong Yin、Yan-Qing Zhang、Biao Jin、Shao Sha、Xun Wu、Chetan B. Sangani、She-Feng Wang、Fang Qiao、Ai-Min Lu、Peng-Cheng Lv、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2015.01.052

  日期：2015.3

  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.
• Tavman, Aydin; Ikiz, Serkan; Bagcigil, A. Funda, Bulletin of the Chemical Society of Ethiopia, 2010, vol. 24, # 3, p. 391 - 400
  作者：Tavman, Aydin、Ikiz, Serkan、Bagcigil, A. Funda、Oezguer, N. Yakut、Ak, Seyyal

  DOI：——

  日期：——
• 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.