1-((2-(pyridin-2-yl)-1H-benzoimidazol-1-yl)methyl)-1H-benzotriazole | 1433996-41-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: 1-((2-(pyridin-2-yl)-1H-benzoimidazol-1-yl)methyl)-1H-benzotriazole
• 英文别名: 1-((2-(pyridin-2-yl)-1-benzoimidazol-1-yl)methyl)-1H-benzotriazole；1-[(2-Pyridin-2-ylbenzimidazol-1-yl)methyl]benzotriazole；1-[(2-pyridin-2-ylbenzimidazol-1-yl)methyl]benzotriazole
• CAS: 1433996-41-8
• 化学式: C₁₉H₁₄N₆
• 分子量: 326.36
• InChiKey: BPTAYHKFLQJNPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  61.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-((2-(pyridin-2-yl)-1H-benzoimidazol-1-yl)methyl)-1H-benzotriazole 、 copper(ll) bromide 以 甲醇 、 氯仿 为溶剂， 反应 72.0h， 以56%的产率得到[(copper(II))2(1-((2-(pyridin-2-yl)-1H-benzoimidazol-1-yl)methyl)-1H-benzotriazole)2(bromide)4]
  参考文献：
  名称：

  金属和结构调整的苯并咪唑基铜锌配合物的体外抗肿瘤活性

  摘要：

  四种新配合物，Cu2(p-2-bmb)2Cl4 (1)、Cu2(p-2-bmb)2Br4 (2)、Zn2(p-3-bmb)2Cl4 (3) 和 [Cu3(p-3) -bmb)2Cl4·(CH3OH)2] n (4)，基于 V 型柔性配体 1-((2-(pyridin-2-yl)-1H-benzoimidazol-1-yl)) 在溶剂热反应下合成甲基）-1H苯并三唑（p-2-bmb）和1-（（2-（吡啶-3-基）-1H-苯并咪唑-1-基）甲基）-1H苯并三唑（p-3-bmb）。配合物 1-3 是双核的，而 4 是具有三金属单元的无限链，然后这些配合物通过 π…π 相互作用和氢键进一步扩展为 3D 超分子结构。这些复合物对四种人类肿瘤细胞系（胃肿瘤细胞系、食管肿瘤细胞系、肝脏肿瘤细胞系、结肠肿瘤细胞系）的体外抗肿瘤活性通过 MTT 测定进行评估。

  DOI：

  10.1080/00958972.2013.789505

文献信息

• In vitro antitumor activity of novel benzimidazole-based Cu(II) complexes
  作者：Jiyong Hu、Yan Guo、Jin'an Zhao、Junshuai Zhang

  DOI：10.1016/j.bmc.2017.08.053

  日期：2017.10

  Cu2(p-2-bmp)2Cl4 (2), Cu2(p-2-bmb)2(DMF)2Br4·(CHCl3) (3), and Cu(p-2-bmb)(NO3)2·(CHCl3) (4) were isolated and characterized, where p-2-bmp is 1-((2-(pyridine-2-yl)-1H-benzoimidazol-1-yl)methyl)-1H-pyridine and p-2-bmb is 1-((2-(pyridin-2-yl)-1-benzoimidazol-1-yl)methyl)-1H-benzotriazole. Complexes 1 and 2 have binuclear configurations, 3 has a mononuclear structure, and 4 has a one-dimensional (1-D) chain

  四种基于苯并咪唑的Cu（II）配合物：Cu 2（p-2-bmp）2 Br 4（1），Cu 2（p-2-bmp）2 Cl 4（2），Cu 2（p-2-bmb） ）2（DMF）2 Br 4 ·（CHCl 3）（3）和Cu（p-2-bmb）（NO 3）2 ·（CHCl 3）（4）进行了分离和表征，其中p-2-bmp是1-（（2-（吡啶-2-基）-1 H-苯并咪唑-1-基）甲基）-1 H-吡啶和p-2-bmb是1-（（2-（吡啶-2-基）-1-苯并咪唑-1-基）甲基）-1 H-苯并三唑。配合物1和2具有双核构型，复合物3具有单核结构，复合物4 具有一维（1-D）链骨架。为了评估它们对人癌细胞的潜在抗癌作用，检测了抗增殖，DNA结合和切割以及凋亡诱导作用。与复合物相比2，3，和4，复杂1表现出强效的体外对四种细胞系（MCF7，EC109，SH-SY5Y和QBC939）具有细胞毒性，其中SH-SY5Y
• Ag/Cd coordination architecture and photoluminescence behaviors
  作者：Jiyong Hu、Yujie Zhao、Fan Yang、Chunli Liao、Jin’an Zhao

  DOI：10.1080/00958972.2018.1467008

  日期：2018.5.3

  are built up from Ag(I)/Cd(II) salts and a flexible pyridyl-benzimidazole-based organic spacer. Single-crystal analysis shows that 1 and 2 have 1-D chains, while 3 displays a tetranuclear structure. All complexes exhibit different coordination geometries and properties, which can be attributed to the difference between the metal centers or anions. In the case of 1 in particular, the Ag⋯Ag interactions

  摘要 三种配位结构，[Ag4(pbmb)4·(BF4)4](CH3OH)2·H2O}n (1), [Cd2(pbmb)4](ClO4)4·(CH3OH)5}n ( 2), 和 [Cd4(pbmb)4·I8(CH3OH)2]n (3) (pbmb = 1-((2-(pyridin-2-yl)-1H-benzoimidazol-1-yl)methyl)-1H -苯并三唑），由 Ag(I)/Cd(II) 盐和灵活的基于吡啶基-苯并咪唑的有机间隔物构成。单晶分析表明，1 和 2 具有一维链，而 3 显示出四核结构。所有配合物都表现出不同的配位几何形状和性质，这可归因于金属中心或阴离子之间的差异。特别是在 1 的情况下，Ag⋯Ag 相互作用在超分子结构的形成中起着至关重要的作用。基于双核的复合物由一对 Ag⋯Ag 触点（约 2.953 Å）组成，它表现出强烈的三线态发射，具有大斯托克斯位移和高热稳定性。与
• Synthesis, chemical nuclease activity, and in vitro cytotoxicity of benzimidazole-based Cu(II)/Co(II) complexes
  作者：Jin-An Zhao、Huai-Bin Yu、Shuang-Cheng Zhi、Rui-Na Mao、Ji-Yong Hu、Xiao-Xiao Wang

  DOI：10.1016/j.cclet.2017.03.025

  日期：2017.7

  carcinoma cell lines, especially complex 1 in the SMMC7721 tumor cell line. Complex 1 was also able to pass through the cell membrane and enter the nucleus and mitochondrion. An analysis of in vitro chemical nuclease activity revealed that complex 1 partially intercalated to calf thymus DNA and exhibited strong unwinding activity against pBR322 superhelical plasmid DNA. The comet assay and flow cytometry

  摘要在这项研究中，新型单/双核Cu（p-2-bmb）（OH）（ClO 4）（1）和Co 2（p-2-bmb）2 Cl 4（2）（p-2-合成并表征了具有氮杂环苯并咪唑的bmb = 1-（（2-（吡啶-2-基）-苯并咪唑-1-基）甲基）-1H-苯并三唑）配合物。两种复合物在各种癌细胞系中均表现出抗增殖作用，尤其是SMMC7721肿瘤细胞系中的复合物1。复合物1也能够穿过细胞膜并进入细胞核和线粒体。体外化学核酸酶活性的分析表明，复合物1部分插入小牛胸腺DNA，并显示出对pBR322超螺旋质粒DNA的强解链活性。彗星分析和流式细胞仪分析证实1引起广泛的DNA损伤，并在细胞周期的G2 / M期将SMMC7721肿瘤细胞停滞，导致线粒体膜电位丧失和细胞凋亡。这些结果表明，这些基于苯并咪唑的金属配合物可能是潜在的抗癌药。
• Photoluminescence and in vitro cytotoxicity of benzimidazole-based CuI/PtII complexes
  作者：Jin’an Zhao、Dandan Zhao、Yang Zhao、Hang Shu、Jiyong Hu

  DOI：10.1016/j.poly.2016.08.004

  日期：2016.11

  Three novel complexes (Cu-2(pzbmb)2(I)2}(n) (1), Pt(pzbmb)(Cl)(2)(DMSO) (2) and Pt(pdbmb)(Cl)(2) (3) based on two novel V-shaped flexible ligands 1((2-(pyrazinyl)-1H-benzoimidazol-1-yl)methyl)-1H-benzotriazole (pzbmb) and 1((2-(pyridine-2-yl)-1H-benzoimidazol-1-yl)methyl)-1H-benzotriazole (pdbmb) have been synthesized under solvothermal conditions. Complex 1 possesses a 1D chain structure with short Cu center dot center dot center dot Cu distance being 3.008 angstrom, whereas complex 2 and 3 are mononuclear motifs. Complexes 1-3 exhibit strong phosphorescence at different temperatures in the range of 13-298 K, which is attributed to the presence of intersystem crossing from singlet to triplet caused by the heavy-atom effect. After being tested against SH-SY5Y (neuroblast tumor cell line) by standard MTT assay, complex 3 displayed promising cytotoxicity. (C) 2016 Elsevier Ltd. All rights reserved.
• Potential anticancer activity of benzimidazole-based mono/dinuclear Zn(II) complexes towards human carcinoma cells
  作者：Jin’an Zhao、Yan Guo、Jiyong Hu、Huaibin Yu、Shuangcheng Zhi、Junshuai Zhang

  DOI：10.1016/j.poly.2015.09.057

  日期：2015.12

  Two Zn(II) complexes bearing benzimidazole-based derivatives, namely Zn-2(p-2-bmb)(2) (NO3)(4) (1) and Zn (p-2-bmp)(2)Cl-2 (2) (p-2-bmb = 1-((2-(pyridin-2-yl)-1-benzoimidazol-1-yl)methyl)-1H-benzotriazole, p-2-bmp = 1-((2-(pyridine-2-yl)-1H-benzoimidazol-1-yl)methyl)-1H-pyridine) were constructed and their biological activities against four human cancer cell lines were estimated. Compared with complex 2, in cytotoxicity research complex I showed higher cytotoxic properties in vitro against different carcinoma cells, especially for SHSY5Y cells. The interactions of complex 1 with calf thymus DNA were studied by spectroscopic techniques, including absorption and fluorescence, which showed the binding mode of 1 is not the classical intercalation binding. The optimum antiproliferative activity of complex I in SHSY5Y cells was found to involve G0/G1 phase arrest of the cell cycle. In addition, the morphological changes and membrane permeability changes also provide evidence that 1 could induce apoptosis. (C) 2015 Elsevier Ltd. All rights reserved.