1-benzyl-2-(4-chlorophenyl)-1H-benzo[d]imidazole | 23982-86-7

• 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: 1-benzyl-2-(4-chlorophenyl)-1H-benzo[d]imidazole
• 英文别名: 1-benzyl-2-(4-chlorophenyl)-1H-benzimidazole；1-benzyl-2-(4-chlorophenyl)benzo[d]imidazole；1-benzyl-2-(4-chloro-phenyl)-1H-benzoimidazole；2-(4-Chlorphenyl)-1-benzyl-benzimidazol；1-Benzyl-2-(4-chlorophenyl)benzimidazole
• CAS: 23982-86-7
• 化学式: C₂₀H₁₅ClN₂
• 分子量: 318.805
• InChiKey: XQVAAXWMDWEOJR-UHFFFAOYSA-N

物化性质

• 熔点：
  137-138 °C
• 沸点：
  511.4±60.0 °C(predicted)
• 密度：
  1.20±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-benzyl-2-(4-chlorophenyl)-1H-benzo[d]imidazole 、 zinc(II) chloride 以 乙醇 为溶剂， 反应 5.0h， 以77%的产率得到dichlorobis(1-benzyl-2-(4-chlorophenyl)-1H-benzimidazole-κN³)zinc(II)
  参考文献：
  名称：

  Synthesis and evaluation of anticancer properties of novel benzimidazole ligand and their cobalt(II) and zinc(II) complexes against cancer cell lines A-2780 and DU-145

  摘要：

  Eighteen new cobalt(II) or zinc(II) complexes of benzimidazole bearing 1-benzyl and 2-phenyl moieties were synthesized from the reaction of appropriate benzimidazole ligands and CoCl2 or ZnCl2. Their structural characterizations were done by IR, NMR (H-1, C-13) and UV-VIS spectrometers. Cytotoxic activities of eighteen new complexes and three benzimidazole ligands were determined using A-2780 (human ovarian) and DU-145 (human prostate) cell lines. Antitumor properties of all compounds were determined by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Cell viability assay for the tested benzimidazole derivatives was performed and the LogIC(50) values of the compounds were calculated after a 24-hour treatment. All tested benzimidazole derivatives showed higher or comparable antitumor activity against A-2780 cell lines compared to the standard drug docetaxel with a LogIC(50) value of -0.81 mu M (p < 0.05). Eight of the examined compounds (1, 3, 5, 6, 7, 9, 10 and 13) showed high cytotoxic activity against A-2780 compared to the standard drug docetaxel. While the LogIC(50) of the docetaxel was -0.81 mu M for A-2780 cells at 24 h, the IC50 values of compounds 1, 3, 5, 6, 7, 9, 10 and 13 were - 0.97, -1.30, - 0.22, 0.13, - 0.16, - 0.73 and - 0.53 mu M, respectively. Three of the compounds 1, 18 and V showed high cytotoxic activity against DU-145 compared to docetaxel (p < 0.05). While the LogIC(50) of the docetaxel was -1.13 mu M for DU-145 cells at 24 h, the LogIC(50) values of compounds 1, 18 and V were 0.84, -0.38 and -0.66 mu M, respectively.

  DOI：

  10.1016/j.ica.2019.118977
• 作为产物：
  描述：

  N-(4-chlorobenzylidene)-N'-phenylhydrazine 在 copper(II) bis(trifluoromethanesulfonate) 、 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 30.0h， 生成 1-benzyl-2-(4-chlorophenyl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  Copper-Mediated Synthesis of Substituted 2-Aryl-N-benzylbenzimidazoles and 2-Arylbenzoxazoles via C–H Functionalization/C–N/C–O Bond Formation

  摘要：

  An efficient method for the transformation of N-benzyl bisarylhydrazones and bisaryloxime ethers to functionalized 2-aryl-N-benzylbenzimidazoles and 2-arylbenzoxazoles is described. The protocol involves a copper(II)-mediated cascade C-H functionalization/C-N/C-O bond formation under neutral conditions. Substrates having either electron-donating or -withdrawing substituents undergo the cyclization to afford the target heterocycles at moderate temperature.

  DOI：

  10.1021/jo2005632

文献信息

• “All-water” chemistry of tandem N-alkylation–reduction–condensation for synthesis of N-arylmethyl-2-substituted benzimidazoles
  作者：Damodara N. Kommi、Dinesh Kumar、Rohit Bansal、Rajesh Chebolu、Asit K. Chakraborti

  DOI：10.1039/c2gc36377a

  日期：——

  also exerts a beneficial effect in the condensation of N-monobenzylated o-phenylenediamines with aldehydes. The water-assisted C–N bond formation chemistry led to metal/base-free synthesis of N-monobenzylated o-nitroanilines and N-monobenzylated o-phenylenediamines. The indispensable/advantageous role of water in the various stage of the N-alkylation–reduction–condensation process exemplifies an ‘all-water’

  设计了水辅助串联N-烷基化-还原-缩合工艺，作为一锅合成N-芳基甲基-2-取代的新合成途径苯并咪唑。 水 通过氢键介导的“亲电-亲核双重”发挥关键和必不可少的作用 激活促进邻硝基苯胺的选择性N-单苄基化，以替代基于过渡金属的C–N键形成（胺化）化学方法，并形成以区域确定的方式将取代基布置在苯并咪唑基团上的基础。水在N-单苄基化邻苯二胺与醛类。水辅助的C–N键形成化学反应导致N /单苄基化的邻硝基苯胺和N-单苄基化的邻苯二胺的无金属/碱合成。的不可或缺/有利的作用水在N-烷基化-还原-缩合过程的各个阶段中，都可以举例说明“全水”化学合成N-芳基甲基-2-取代基的过程苯并咪唑。
• “All-water” one-pot diverse synthesis of 1,2-disubstituted benzimidazoles: hydrogen bond driven ‘synergistic electrophile–nucleophile dual activation’ by water
  作者：Damodara N. Kommi、Pradeep S. Jadhavar、Dinesh Kumar、Asit K. Chakraborti

  DOI：10.1039/c3gc37004f

  日期：——

  promoting the subsequent nitro reduction and in the final cyclocondensation steps. The role of water in promoting the cyclocondensation reaction through hydrogen bonds is realized by the differential product yields during the reaction of mono-N-phenyl-o-phenylenediamine with benzaldehyde performed separately in water and D2O. The better hydrogen bond donor and hydrogen bond acceptor abilities of water

  新的“全水”串联芳基氨基芳基化/芳基氨基烷基化–还原–环化 报道了一锅多样性导向的区域定义的1,2-二取代的合成路线 苯并咪唑。 水 通过氢键驱动的'协同亲电试剂-亲核试剂双重作用，起着至关重要的和必不可少的作用 激活在形成N-单-芳基/芳基烷基/烷基/环烷基 在无金属和无碱条件下邻硝基苯胺取代基于过渡金属的C–N键的形成（芳基 胺化）的化学成分，并强调了区域定义安装的起源，包括多种选择 芳基，芳基烷基和 烷基/环烷基作为苯并咪唑支架上的取代基以形成1,2-二取代 苯并咪唑。氢键效应的影响水通过观察D 2 O的收率低于在D 2 O中获得的收率，已经实现了在无碱和无金属条件下促进芳基氨基芳基化反应的研究。水 在反应过程中 邻氟硝基苯 和 苯胺 单独执行 水和D 2 O在相似的实验条件下。水 还提供了促进后续硝化的帮助 减少并在最后的循环冷凝步骤中。的作用水 通过氢键促进环缩合反应的过程是通过反应过程中产物收率的差异来实现的
• One-pot strategy of copper-catalyzed synthesis of 1,2-disubstituted benzimidazoles
  作者：Caixia Xie、Xushuang Han、Jian Gong、Danyang Li、Chen Ma

  DOI：10.1039/c7ob00945c

  日期：——

  A simple, one-pot and copper-catalyzed coupling reaction for the construction of 1,2-disubstituted benzimidazole derivatives is described. Low-cost copper salt and weak base K3PO4 were utlized in this reaction. A variety of 1,2-disubstituted benzimidazoles were obtained in moderate to excellent yields.

  描述了一种简单的，一锅法和铜催化的偶联反应，用于构建1,2-二取代的苯并咪唑衍生物。在该反应中使用了廉价的铜盐和弱碱K3PO4。以中等至优异的产率获得了各种1,2-二取代的苯并咪唑。
• Selective Synthesis of 2-Substituted and 1,2-Disubstituted Benzimidazoles Directly from Aromatic Diamines and Alcohols Catalyzed by Molecularly Defined Nonphosphine Manganese(I) Complex
  作者：Kalicharan Das、Avijit Mondal、Dipankar Srimani

  DOI：10.1021/acs.joc.8b01316

  日期：2018.8.17

  Herein, we present a selective synthesis of 2-substituted and 1,2-disubstituted benzimidazoles by acceptorless dehydrogenative coupling of aromatic diamine with primary alcohols. The reaction is catalyzed by a phosphine-free tridentate NNS ligand-derived manganese(I) complex.

  在这里，我们介绍了通过芳族二胺与伯醇的无受体脱氢偶联选择性合成2取代和1，2-二取代的苯并咪唑。该反应由不含膦的三齿NNS配体衍生的锰（I）配合物催化。
• <i>N</i>,2,6-Trisubstituted 1<i>H</i>-benzimidazole derivatives as a new scaffold of antimicrobial and anticancer agents: design, synthesis, <i>in vitro</i> evaluation, and <i>in silico</i> studies
  作者：Em Canh Pham、Tuong Vi Le Thi、Huong Ha Ly Hong、Bich Ngoc Vo Thi、Long B. Vong、Thao Thanh Vu、Duy Duc Vo、Ngoc Vi Tran Nguyen、Khanh Nguyen Bao Le、Tuyen Ngoc Truong

  DOI：10.1039/d2ra06667j

  日期：——

  2-arylbenzimidazole derivatives followed by N-alkylation by conventional heating or microwave irradiation for diversification. Potent antibacterial compounds against MSSA and MRSA were discovered such as benzimidazole compounds 3k (2-(4-nitrophenyl), N-benzyl), 3l (2-(4-chlorophenyl), N-(4-chlorobenzyl)), 4c (2-(4-chlorophenyl), 6-methyl, N-benzyl), 4g (2-(4-nitrophenyl), 6-methyl, N-benzyl), and 4j (2-(4-nitrophenyl)

  含有苯并咪唑部分的化合物在发现新的生物活性物质方面占据着优越的化学空间。继续我们最近的工作，使用有效的合成方案（即焦亚硫酸钠催化芳香醛与邻苯二胺缩合形成 2-芳基苯并咪唑衍生物，然后形成N- ），设计并合成了 69 种苯并咪唑衍生物，收率高达 46-99%。通过常规加热或微波辐射进行烷基化以实现多样化。发现了针对 MSSA 和 MRSA 的有效抗菌化合物，例如苯并咪唑化合物3k (2-(4-硝基苯基), N-苄基), 3l (2-(4-氯苯基), N- (4-氯苄基)), 4c (2 -(4-氯苯基)，6-甲基， N-苄基)， 4g (2-(4-硝基苯基)，6-甲基， N-苄基)，和4j (2-(4-硝基苯基)，6-甲基， N- (4-氯苄基))，MIC 为 4–16 μg mL -1 。此外，化合物4c对大肠杆菌和粪链球菌表现出良好的抗菌活性（MIC = 16 μg mL -1 ）。此外，化合物3k