1,4-bis(benzimidazol-1-yl)-2-butylene

• 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: 1,4-bis(benzimidazol-1-yl)-2-butylene
• 英文别名: 1,4-bis(benzimidazol-1-yl)-2-butene；1-[4-(Benzimidazol-1-yl)but-2-enyl]benzimidazole；1-[4-(benzimidazol-1-yl)but-2-enyl]benzimidazole
• 化学式: C₁₈H₁₆N₄
• 分子量: 288.352
• InChiKey: FNFICXIAXXQSTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  35.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-萘二甲酸 、 1,4-bis(benzimidazol-1-yl)-2-butylene 、 zinc(II) acetate dihydrate 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 72.0h， 以56.4%的产率得到[Zn(1,4-bis(benzimidazol-1-yl)-2-butylene)0.5(1,4-naphthalenedicarboxylic acid)]_n
  参考文献：
  名称：

  两个水稳定的基于Zn（II）的MOF作为高选择性发光探针，可双重检测水溶液中的乙二醛和重铬酸根离子

  摘要：

  两种新的水稳定性锌金属有机骨架（Zn-MOF）配制成[Zn（L1）（1,4-NDC）] n（1）和[Zn（L2）0.5（1,4-NDC）] n（2）（L1 = 1,4-双（5,6-二甲基苯并咪唑-1-基）-2-丁烯，L2 = 1,4-双（苯并咪唑-1-基）-2-丁烯，1,4-合成并表征了H 2 NDC ＝ 1，4-萘二甲酸。1具有不寻常的3D（3,4）连接的dmc拓扑结构，2具有很少的2倍互穿3D（4,5）连接的xah框架。1和2可用作双重发光探针，用于检测乙二醛和Cr水中的2 O 7 2−阴离子，具有很高的灵敏度，选择性和可回收性。还介绍了感测乙二醛和Cr 2 O 7 2-的机理。首次展示了基于MOF材料的氟传感器，可以有效地感测乙二醛。

  DOI：

  10.1016/j.jssc.2019.07.052

文献信息

• Synthesis, antimicrobial and antiproliferative activities of new self-assembly benzimidazole-bridged aren ruthenium rectangles in human breast cancer cells
  作者：Ersin Orhan、Görkem Dülger、Merve Alpay、Nilüfer Öksüz、Başaran Dülger

  DOI：10.1007/s10847-021-01099-x

  日期：2022.2

  Some novel benzimidazole-bridged aren ruthenium rectangle compounds of the general structure [Ru2(p-cymene)2(µ4-OO∩OO)}2(µ4-bbim)]4+ (bbim = 1,1′-butyl-2-ene-di(benzimidazole) were obtained from the corresponding double-nuclear arene ruthenium compounds [Ru2(p-cymene)2(µ4-OO∩OO)Cl2] (OO∩OO = 2,5-dioxido-1,4-benzoquinonato (dobq), 2,5-dichloro-1,4-benzoquinonato (dClbq), 2,5-dibromo-1,4-benzoquinonato (dBrbq), oxalato (oxa), and 5,8-dioxido-1,4-naphtoquinonato (donq) via reaction with the bbim molecule and AgCF3SO3. The antiproliferative activity and anti-cancer properties of the tetranuclear arene ruthenium compounds were evaluated against the human breast cancer cell line (MDA-231-MB). Compound 2 showed the highest antiproliferative effect among the compounds during 24- and 48-h administration. In addition, all other compounds exhibited very good cancer cell selectivity and very low micromolar cytotoxicity. The antimicrobial activities of the synthesized compounds were also determined against various test microorganisms. Evaluations were carried out using the disk diffusion method and the dilution method. In particular, the compounds exhibited more potential antibacterial effects against Gram negative bacteria than against Gram positive bacteria and showed a superior antifungal effect against Candida species. The results revealed the benzimidazole-bridged aren ruthenium rectangle compounds to be very strong and potent inhibitors.

  从相应的双核炔钌化合物[Ru2(p-cymene)2(µ4-OO∩OO)}2(µ4-bbim)]4+（bbim = 1、1′-butyl-2-ene-di(benzimidazole) 从相应的双核芴钌化合物 [Ru2(p-cymene)2(µ4-OO∩OO)Cl2] 中得到（OO∩OO = 2、Cl2]（OO∩OO = 2,5-二氧代-1,4-苯醌（dobq）、2,5-二氯-1,4-苯醌（dClbq）、2,5-二溴-1,4-苯醌（dBrbq）、草酸（oxa）和 5,8-二氧代-1,4-萘醌（donq））。研究人员评估了四核芳香族钌化合物对人类乳腺癌细胞系（MDA-231-MB）的抗增殖活性和抗癌特性。在给药 24 和 48 小时期间，化合物 2 的抗增殖效果最高。此外，所有其他化合物都具有很好的癌细胞选择性和很低的微摩尔细胞毒性。还测定了合成化合物对各种测试微生物的抗菌活性。评估采用了盘扩散法和稀释法。特别是，这些化合物对革兰氏阴性菌的潜在抗菌效果优于对革兰氏阳性菌的抗菌效果，对白色念珠菌的抗真菌效果也更出色。研究结果表明，苯并咪唑桥接钌矩形化合物是一种非常强效的抑制剂。
• Two Zn(II)‐based meta‐organic frameworks: Selective detection of antibiotics and treatment activity on age‐related macular degeneration by reducing inflammasome activation
  作者：Ya Zhang、Fei Sun、Hua Liu

  DOI：10.1002/jccs.202000193

  日期：2021.1

  room temperature, complex 2 has the high selectivity and sensibility of fluorescence detection to the ceftriaxone sodium (a kind of antibiotic) with the detection limit up to ppm lever. The treatment activity of the compounds on age‐related macular degeneration was assessed and the specific mechanism was investigated. First of all, the inflammasome activation in the endothelial cells of retina was evaluated

  通过使用混合配体方法，两个化学式为[Zn（L）（5-HIP）]·H 2 O} n（1）和[Zn（II）的新型含Zn（II）的有机骨架。L）（2,6-NDC）] n（2）是在溶剂热条件下通过应用芳香族二羧酸配体制备的（5-H 2 HIP = 5-羟基间苯二甲酸; 2,6-H 2 NDC = 2,6-萘二甲酸）和1,4-双（苯并咪唑-1-基）-2-丁烯（L）。由于其良好的水稳定性以及室温下强烈的发光，复合物2对头孢曲松钠（一种抗生素）的荧光检测具有很高的选择性和灵敏度，检测极限高达ppm级。评估了这些化合物对与年龄有关的黄斑变性的治疗活性，并研究了其具体机制。首先，用蛋白质印迹法评价视网膜内皮细胞中的炎性小体活化。除此之外，还使用ELISA检测试剂盒测量了炎性体激活的下游产生。
• A dual-responsive luminescent sensor based on a water-stable Cd(<scp>ii</scp>)-MOF for the highly selective and sensitive detection of acetylacetone and Cr₂O₇²⁻ in aqueous solutions
  作者：Ying-Jie Yang、Yue-Hua Li、Dong Liu、Guang-Hua Cui

  DOI：10.1039/c9ce01546a

  日期：——

  Two water-stable cadmium(ii) MOFs were synthesized and characterized. 1 is the first dual-function Cd(ii)-MOF luminescent sensor for sensing acetylacetone and Cr₂O₇²⁻ in aqueous solution with high sensitivity and selectivity and good recyclability.

  合成并表征了两种水稳定的镉(ii)金属有机框架(MOFs)。1是第一个双功能Cd(ii)-MOF发光传感器，可在水溶液中高灵敏度、高选择性地检测乙酰丙酮和Cr₂O₇²⁻，并具有良好的可重复使用性。
• Visible-light-driven photocatalysts of three nickel(II) coordination polymers with mixed ligands
  作者：Shao Yun Hao、Suo Xia Hou、Jing Zhu、Guang Hua Cui

  DOI：10.1016/j.poly.2017.06.003

  日期：2017.9

  Three ternary mixed-ligand Ni(II) coordination polymers (CPs) including [Ni(DCTP)(L1)center dot(H2O)(2)]center dot(H2O)} (1), [Ni(DCTP)(L2)center dot(H2O)(2)] (2), and [Ni(DCTP)(L3)] (3) (L1 = 1,4-bis(benzimidazol-1-y1)-2-butene, L2 = 1,4-bis(imidazol-1-ylmethyl)benzene, 13 = 1,4-bis(5,6-dimethylbenzimidazol-1-ylmethyl)benzene, H2DCTP = 2,5-dichloroterephthalic acid), have been synthesized with a hydrothermal technique and structurally characterized by single-crystal X-ray diffraction, infrared spectroscopy, powder X-ray diffraction, and thermogravimetric analysis. Both CPs 1 and 2 display 2D 4-connected sql sheets, CP 1 exhibits a 2D 13(9)2(4) water layer interconnected by hydrogen bonding interactions, CP 2 is further extended into a 3D supramolecular framework through O-H center dot center dot center dot O hydrogen bonding interactions. CP 3 reveals a 3D 3 fold interpenetrated 4-connected dia framework with the point symbol 6(6)}. Crystal packing analysis well indicates that O-H center dot center dot center dot O and C-H center dot center dot center dot pi are the most intermolecular interactions in CPs 1-2. Furthermore, the electrochemical properties of CPs 1-3 were discussed in detail. Notably, CPs 1-3 represented the rare examples of Ni(II) CPs materials as visible-light-driven photocatalysts and showed high activities for degradation of Methyl Blue. (C) 2017 Published by Elsevier Ltd.
• Two new luminescent ternary Cd(II)-MOFs by regulation of aromatic dicarboxylate ligands used as efficient dual-responsive sensors for toxic metal ions in water
  作者：Ying-Jie Yang、Dong Liu、Yue-Hua Li、Gui-Ying Dong

  DOI：10.1016/j.poly.2018.11.051

  日期：2019.2

  Two new Cd(lI) metal-organic frameworks (MOFs) formulated as [Cd(L)(atpa)](n) (1) and [Cd(L)(tbta) (H2O)](n) (2) [H(2)atpa = 2-aminoterephthalic acid, H(2)tbta = tetrabromoterephthalic acid, L = 1,4-bis(benz-imidazol-1-yl)-2-butene] were hydrothermally synthesized. 1-2 were characterized by IR spectroscopy, elemental analysis, and single-crystal X- ray diffraction. 1 displays a 3D framework with five-fold interpenetrating dia topology. 2 holds a 2D corrugated sql layer. Both MOFs were confirmed to be dual-responsive luminescent sensors (Cu2+ and Cr2O72- for 1, Hg2+ and Cr2O72- for 2) in water through the luminescence quenching experiments. The detection limits for these species were 1.2 mu M (Cu2+) and 0.29 mu M (Cr2O72-) of 1, 0.043 mu M (Hg2+) and 0.13 mu M (Cr2O72-) of 2, respectively. The luminescence quenching mechanism was investigated. (C) 2018 Elsevier Ltd. All rights reserved.