2-(1-苯基苯并咪唑-2-基)乙腈 | 6468-35-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 2-(1-苯基苯并咪唑-2-基)乙腈
• 英文名称: 2-cyanomethyl-N-phenylbenzimidazole
• 英文别名: 2-(1-phenyl-1H-benzo[d]imidazol-2-yl)acetonitrile；1-Phenyl-2-cyanmethyl-benzimidazol；2-cyanomethyl-1-phenyl-1H-benzimidazole；2-(1-phenylbenzimidazol-2-yl)acetonitrile
• CAS: 6468-35-5
• 化学式: C₁₅H₁₁N₃
• 分子量: 233.272
• InChiKey: PUVJNGYMBOVTNS-UHFFFAOYSA-N

物化性质

• 熔点：
  112 °C
• 沸点：
  456.4±47.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  41.6
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-(1-苯基苯并咪唑-2-基)乙腈 在 哌啶 、 碘 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 4-chloro-5-phenylbenzimidazo[1,2-a]quinoline-6-carbonitrile
  参考文献：
  名称：

  Synthesis, crystal structure and spectroscopic study of novel benzimidazoles and benzimidazo[1,2-a]quinolines as potential chemosensors for different cations

  摘要：

  In this manuscript the synthesis, crystal structure, spectroscopic characterization and titration with several metal chloride salts of novel E-3-phenyl-2-(1-phenylbenzimidazol-2-yl)acrylonitriles and 5-phenylbenzimidazo[1,2-a]quinoline derivatives are described. All compounds were characterized by means of H-1, C-13 NMR, MS, UV/Vis and fluorescence spectroscopy.Crystal and molecular structures of E-3-(4-nitrophenyl)-2-(1-phenyl-benzimidazol-2-yl)acrylonitrile and 5-phenylbenzimidazo[1,2-a]quinoline-6-carbonitrile were determined by single-crystal X-ray diffractometry. The molecular assembly is characterized by the C-H center dot center dot center dot-O and C-H center dot center dot center dot N intermolecular hydrogen bonds in E-3-(4-nitrophenyl)-2-(1-phenyl-benzimidazol-2-yl)acrylonitrile and 5-phenylbenzimidazo [1,2-a]quinoline-6-carbonitrile, respectively.Spectroscopic characterization of the prepared compounds was performed by using UV/Vis and fluorescence spectroscopy in ethanol. In order to determine a selectivity towards a variety of cations, to explore their use as potential chemosensors, the amino substituted 5-phenylbenzimidazo[1,2-a]quinoline-6-carbonitrile was chosen for a titration with metal chloride salts using fluorescence spectroscopy. The fluorescence intensity significantly increased upon addition of Zn2+ and Ag+ cations while decreased by addition of Mn2+, Co2+, Cu2+, Hg+, Li+ and Fe3+ cations. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2012.05.024
• 作为产物：
  描述：

  N-Cyanoacetyl-2-nitro-diphenylamin 以79%的产率得到
  参考文献：
  名称：

  HARA T.; FUJIMORI H.; KAYAMA Y.; MORI T.; ITOH K.; HASHIMOTO Y., CHEM. AND PHARM. BULL. , 1977, 25, NO 10, 2584-2592

  摘要：

  DOI：

文献信息

• <i>N</i>,<i>O</i>-Bidentate ligand-tunable copper(<scp>ii</scp>) complexes as a catalyst for Chan–Lam coupling reactions of arylboronic acids with 1<i>H</i>-imidazole derivatives
  作者：Xuefeng Jia、Pai Peng

  DOI：10.1039/c8ob02254b

  日期：——

  An efficient procedure for Chan–Lam coupling reactions of arylboronic acids with 1H-imidazole derivatives using N,O-bidentate ligand-tunable copper(II) complexes as a catalyst under base-free conditions has been developed. This protocol features mild reaction conditions, high yields and compatibility with different functional groups, providing a direct and facile strategy for the construction of C–N

  已经开发了一种有效的程序，用于在无碱条件下使用N，O-双齿配体可调铜（II）配合物作为催化剂，使芳基硼酸与1 H-咪唑衍生物进行Chan-Lam偶联反应。该方案具有温和的反应条件，高收率和与不同官能团的相容性，为构建C–N键和合成杂环化合物提供了直接而简便的策略。
• N-substituted benzimidazole acrylonitriles as in vitro tubulin polymerization inhibitors: Synthesis, biological activity and computational analysis
  作者：N. Perin、L. Hok、A. Beč、L. Persoons、E. Vanstreels、D. Daelemans、R. Vianello、M. Hranjec

  DOI：10.1016/j.ejmech.2020.113003

  日期：2021.2

  antiproliferative activity in vitro on eight human cancer cell lines and one reference non-cancerous assay. N,N-dimethylamino substituted acrylonitriles 30 and 41, bearing N-isobutyl and cyano substituents placed on the benzimidazole nuclei, showed strong and selective antiproliferative activity in the submicromolar range of inhibitory concentrations (IC50 0.2 – 0.6 μM), while being significantly less

  我们提出了新型的N-取代的苯并咪唑基丙烯腈作为微管蛋白聚合的潜在抑制剂的设计，合成和生物活性。它们的合成是使用经典的线性有机和微波辅助技术完成的，从芳香醛和N-取代的2-氰基甲基苯并咪唑类化合物开始。所有新制备的化合物均在八种人类癌细胞系中进行了体外抗增殖活性的测试，并在一项非癌性参考测定中进行了测试。N，N-二甲基氨基取代的丙烯腈30和41，含N苯并咪唑核上的-异丁基和氰基取代基在亚微摩尔浓度的抑制浓度下（IC 50 0.2 – 0.6μM）显示出强而有选择性的抗增殖活性，但毒性明显低于参考系统多西他赛和星形孢菌素，因此促进它们作为铅化合物。作用机理研究表明，两种活性最高的化合物抑制微管蛋白的聚合。计算分析证实所用的苯并咪唑-丙烯腈骨架适合于微管蛋白中秋水仙碱结合位点内的结合，从而使观察到的抗肿瘤活性合理化，并证明了E-异构体是活性物质。它还提供了影响结合位置和匹配亲和力的结构决定因素，确定了附着的NMe
• Antiulcer fused imidazole compounds
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US04563455A1

  公开（公告）日：1986-01-07

  New fused imidazole compounds of the formula: ##STR1## wherein A is lower alkylene, R.sup.1 is hydrogen, lower alkyl, lower alkoxy or halogen, R.sup.2 is hydrogen, lower alkyl, cyclo(lower)alkyl, pyridyl, ar(lower)alkyl which may be substituted with halogen, or aryl which may be substituted with lower alkyl, lower alkoxy, hydroxy or halogen, R.sup.3 is N-containing unsaturated heterocyclic group which may be substituted with lower alkyl or amino, and Y is .dbd.C-- or .dbd.N--, and pharmaceutically acceptable salts thereof, and processes for preparation thereof and pharmaceutical composition comprising the same. These derivatives and salts thereof are useful as antiulcer agents.

  新的融合咪唑化合物的化学式如下：##STR1## 其中A为较低的烷基，R.sup.1为氢、较低的烷基、较低的烷氧基或卤素，R.sup.2为氢、较低的烷基、环(较低)烷基、吡啶基、含氮的不饱和杂环基，可以用卤素取代的芳基或被较低的烷基、较低的烷氧基、羟基或卤素取代的芳基，R.sup.3为可能用较低的烷基或氨基取代的含氮不饱和杂环基，Y为.dbd.C--或.dbd.N--，以及其药学上可接受的盐，以及其制备方法和包含它们的药物组合物。这些衍生物及其盐可用作抗溃疡药物。
• Synthesis, Computational Analysis, and Antiproliferative Activity of Novel Benzimidazole Acrylonitriles as Tubulin Polymerization Inhibitors: Part 2
  作者：Anja Beč、Lucija Hok、Leentje Persoons、Els Vanstreels、Dirk Daelemans、Robert Vianello、Marijana Hranjec

  DOI：10.3390/ph14101052

  日期：——

  colchicine binding site in tubulin. In addition, it also underlined that higher tubulin affinities are linked with (i) bulkier alkyl and aryl moieties on the benzimidazole nitrogen and (ii) electron-donating substituents on the phenyl group that allow deeper entrance into the hydrophobic pocket within the tubulin’s β-subunit, consisting of Leu255, Leu248, Met259, Ala354, and Ile378 residues.

  我们使用经典的线性和微波辅助合成方法制备了新型N-取代的苯并咪唑衍生的丙烯腈，其在体外对多种癌细胞具有抗增殖活性。最有效的系统对所有测试的血液癌细胞系均表现出显着的活性，并对正常细胞具有良好的选择性。还对先导化合物的选择进行了体外测试，以抑制微管蛋白聚合，作为可能的生物作用机制。对接和分子动力学模拟的结合证实了所采用的有机骨架对于抗肿瘤药物设计的适用性，并证明其生物活性依赖于与微管蛋白中秋水仙碱结合位点的结合。此外，它还强调，较高的微管蛋白亲和力与（i）苯并咪唑氮上较大的烷基和芳基部分以及（ii）苯基上的供电子取代基有关，这些取代基允许更深入地进入微管蛋白β-内的疏水口袋。亚基，由 Leu255、Leu248、Met259、Ala354 和 Ile378 残基组成。
• Benzimidazole acrylonitriles as multifunctional push-pull chromophores: Spectral characterisation, protonation equilibria and nanoaggregation in aqueous solutions
  作者：Ema Horak、Robert Vianello、Marijana Hranjec、Svjetlana Krištafor、Grace Karminski Zamola、Ivana Murković Steinberg

  DOI：10.1016/j.saa.2017.02.011

  日期：2017.5

  pH sensitivity and compatibility with biomolecules. The photophysical characterisation of the prototropic forms of these chromophores has been carried out in both solution and on immobilisation in polymer films. The experimental results are further supported by computational determination of pKa values. It is noticed that compound 3 forms nanoaggregates in aqueous solutions with aggregation-induced

  杂环供体- π基于一个端受体分子系统Ñ，ñ -二甲基氨基苯基丙烯腈的苯并咪唑骨架已被表征并提出了潜在用途在传感应用。苯并咪唑部分为系统引入了广泛的有用多功能特性，包括电子接受能力，pH敏感性和与生物分子的相容性。这些生色团的质子形式的光物理表征已经在溶液中和固定在聚合物膜中进行。通过计算确定p K a值进一步支持了实验结果。注意到化合物3在水溶液中以600 nm的聚集诱导发射（AIE）形式形成纳米聚集体。所有系统都证明了在酸性介质中的光谱pH敏感性，当固定在聚合物薄膜中或在水性环境中聚集时（化合物3），pH敏感性接近中性值。已经确定了这些功能性发色团的结构-性质关系，包括其光谱特征，酸碱平衡，p K a值和聚集效应。基于分子的pH敏感性和AIE特性，提出了分子作为pH和生物分子传感器的潜在应用。