N-((1H-benzo[d]imidazol-2-yl)methyl)-4-bromoaniline | 772294-44-7

• 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: N-((1H-benzo[d]imidazol-2-yl)methyl)-4-bromoaniline
• 英文别名: (1H-benzimidazol-2-ylmethyl)-N-(4-bromophenyl)amine；N-(1H-benzimidazol-2-ylmethyl)-4-bromoaniline
• CAS: 772294-44-7
• 化学式: C₁₄H₁₂BrN₃
• 分子量: 302.173
• InChiKey: BSENJYJKZIJUNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  40.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氯甲基苯并咪唑 、 4-溴苯胺 在 sodium iodide 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 N-((1H-benzo[d]imidazol-2-yl)methyl)-4-bromoaniline
  参考文献：
  名称：

  探索一些生物活性苯并咪唑衍生物的电子结构和取代效应：实验见解和 DFT 计算

  摘要：

  摘要 一系列 (1H-苯并咪唑-2-基甲基)-N-(4-苯基)胺衍生物结合不同的给电子和吸电子基团 (X = 4 OCH3 (1), 4 CH3 (2), H (3)制备、表征和筛选了苯基取代基的对位上的 、 4 Cl (4) 和 4 Br (5)) 对某些微生物的潜在抗菌活性。通过与哈米特常数拟合，可以很好地确定取代基对光谱数据（振动模式和 NMR 共振）的影响。未取代的衍生物 4 对金黄色葡萄球菌表现出与标准四环素 (MIC = 0.18 μM) 相当的活性 (MIC = 0.26 μM)。在苯环上引入取代基导致抗菌活性降低。通过TDDFT计算研究了取代基对1-5电子结构的影响。可电离的 NH 基团的酸解离常数与 Kubota 的 σ− 参数（R2 = 0.9196）密切相关。通过线性溶剂化-能量关系方程分析研究了1-5在不同极性和氢键趋势的溶剂中的溶剂化变色行为。进行了各种量子化学描

  DOI：

  10.1016/j.molstruc.2020.128996

文献信息

• Novel palladium(II) and platinum(II) complexes with 1H-benzimidazol-2-ylmethyl-N-(4-bromo-phenyl)-amine: Structural studies and anticancer activity
  作者：Nour T. Abdel Ghani、Ahmed M. Mansour

  DOI：10.1016/j.ejmech.2011.11.008

  日期：2012.1

  [MLCl2] (L = (1H-benzimidazol-2-ylmethyl)-N-(4-bromo-phenyl)-amine; M = Pd & Pt) and [PdL(OH2)(2)]center dot 2X center dot zH(2)O (X = Br, I, z = 2; X = SCN, z = 1; X = NO3, z = 0) complexes have been synthesized as potential anticancer compounds and their structures were elucidated using elemental analysis, spectral, thermal analysis and X-ray powder diffraction. The benzimidazole (L) crystallizes in the space group P2(1)/c with a = 8.6660(3) angstrom, b = 16.6739(7) angstrom, c = 9.8611(4) angstrom and beta = 113.505(3)degrees and forms an infinite chain structure with a trans-zigzag type along the crystallographic axis "a", through the intermolecular H bond. FT-IR and H-1 NMR studies revealed that the ligand L is coordinated to the metal ion via the pyridine-type nitrogen (N-py) of the benzimidazole ring and secondary amino group (NHsec). Quantum mechanical calculations of energies, geometries, vibrational wavenumbers, and H-1 NMR of the benzimidazole L and its complexes were carried out by DFT/B3LYP method combined with 6-31G(d) and LANL2DZ basis sets. Natural bond orbital (NBO) analysis and frontier molecular orbitals (FMO) were performed at B3LYP/LANL2DZ level of theory. The benzimidazole L, in comparison to its metal complexes was screened for its antibacterial activity. The complexes showed cyctotoxic effects against human breast cancer (MCF7), hepatocarcinoma (HepG(2)) and colon carcinoma cells (HCT). The platinum complex (6) exhibited a moderate antitumor activity against MCF7 with IC50 = 10.2 mu M comparing to that reported for cis-platin 9.91 mu M. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Exploring electronic structure, and substituent effect of some biologically active benzimidazole derivatives: Experimental insights and DFT calculations
  作者：Ola R. Shehab、Ahmed M. Mansour

  DOI：10.1016/j.molstruc.2020.128996

  日期：2021.1

  groups (X = 4 OCH3 (1), 4 CH3 (2), H (3), 4 Cl (4), and 4 Br (5)) on the para-position of the phenyl substituent was prepared, characterized and screened for their potential antimicrobial activity against some microbes. The substituent effect on the spectroscopic data (vibrational modes and NMR resonances) is well established by fitting with the Hammett constant. The unsubstituted derivative 4 exhibited

  摘要 一系列 (1H-苯并咪唑-2-基甲基)-N-(4-苯基)胺衍生物结合不同的给电子和吸电子基团 (X = 4 OCH3 (1), 4 CH3 (2), H (3)制备、表征和筛选了苯基取代基的对位上的 、 4 Cl (4) 和 4 Br (5)) 对某些微生物的潜在抗菌活性。通过与哈米特常数拟合，可以很好地确定取代基对光谱数据（振动模式和 NMR 共振）的影响。未取代的衍生物 4 对金黄色葡萄球菌表现出与标准四环素 (MIC = 0.18 μM) 相当的活性 (MIC = 0.26 μM)。在苯环上引入取代基导致抗菌活性降低。通过TDDFT计算研究了取代基对1-5电子结构的影响。可电离的 NH 基团的酸解离常数与 Kubota 的 σ− 参数（R2 = 0.9196）密切相关。通过线性溶剂化-能量关系方程分析研究了1-5在不同极性和氢键趋势的溶剂中的溶剂化变色行为。进行了各种量子化学描