(1-benzyl-1H-benzoimidazol-2-yl)-acetonitrile | 7711-26-4

• 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-1H-benzoimidazol-2-yl)-acetonitrile
• 英文别名: 1-Benzyl-2-cyanmethyl-benzimidazol；1-Benzyl-1h-benzimidazol-2-ylacetonitrile；2-(1-benzylbenzimidazol-2-yl)acetonitrile
• CAS: 7711-26-4
• 化学式: C₁₆H₁₃N₃
• 分子量: 247.299
• InChiKey: WPTJUBYDXYXYRI-UHFFFAOYSA-N

物化性质

• 沸点：
  489.9±38.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  41.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1-benzyl-1H-benzoimidazol-2-yl)-acetonitrile 以 N,N-二甲基甲酰胺 为溶剂， 生成 6-amino-7-(1-benzyl-1H-benzo[d]imidazol-2-yl)-5-(2-furylmeth yl)-5H-pyrrolo[2,3-dicarbonitrile
  参考文献：
  名称：

  Novel 5,7-disubstituted 6-amino-5H-pyrrolo[3,2-b]pyrazine-2,3-dicarbonitriles, the promising protein kinase inhibitors with antiproliferative activity

  摘要：

  New derivatives of pyrrolo[2,3-b]pyrazine were synthesized and tested on a panel of cultured human tumor cell lines. It was found that 6-amino-5-(3-chlorophenylamino)-7-(1-methyl-1H-benzo[dlimidazol-2-yl]-5H-pyrrolo[3,2-b]pyrazine-2,3-dicarbonitrile (4j) exhibited a significant antiproliferative activity: GI50 for cell lines RXF 393 (renal cancer) and BT-549 (breast cancer) were 14 and 82 nM, respectively. To identify possible molecular targets, docking of the most active compounds into the active sites of cyclin-dependent kinases was performed. Molecular modeling of the inhibitor-enzyme complexes showed the differences in the binding poses of new pyrrolo[2,3-b]pyrazine derivatives in the kinase ATP-binding site compared with known pyrrolo[2,3-b]pyrazine inhibitors called aloisines. The patterns of drug kinase interactions correlated well with antiproliferative activities of novel derivatives. Key interactions and binding mode of docked compounds are discussed. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.03.019
• 作为产物：
  描述：

  N1-苄基苯-1,2-二胺 、 氰乙酸乙酯 在 甲烷磺酸 作用下， 以 乙二醇 为溶剂， 反应 4.0h， 以75%的产率得到(1-benzyl-1H-benzoimidazol-2-yl)-acetonitrile
  参考文献：
  名称：

  PYRAZOLOTRIAZINES AS INHIBITORS OF NUCLEASES

  摘要：

  公开号：

  EP2957562B1

文献信息

• Interaction of 2-chloroquinoline- 3-carbaldehydes with 2-hetaryl- acetonitriles
  作者：T. A. Volovnenko、A. V. Tarasov、R. I. Zubatyuk、O. V. Shishkin、A. V. Turov、Yu. M. Volovenko

  DOI：10.1007/s10593-010-0456-7

  日期：2009.12

  shown that products of condensation at the methylene group are formed under mild conditions. Carrying out the reaction under more forcing conditions leads to an intramolecular nucleophilic substitution of the chlorine atom and the formation of cyclic ionic compounds (in the case of N-substituted hetarylacetonitriles), which are subsequently dealkylated.

  研究了2-氯喹啉-3-甲醛与1H-苯并咪唑-2-基乙腈和1-苄基-1H-咪唑-2-基乙腈的相互作用。结果表明，在温和条件下会形成亚甲基缩合产物。在更强的条件下进行反应导致氯原子的分子内亲核取代和形成环状离子化合物（在N-取代的杂芳基乙腈的情况下），随后将其脱烷基化。
• Pyrazolotriazines as inhibitors of nucleases
  申请人：Masarykova univerzita

  公开号：EP2957562A1

  公开（公告）日：2015-12-23

  The invention provides compounds represented by the structural formula (1): wherein R1, R2, R3 and R4 are as defined in the claims. The compounds are inhibitors of nucleases, and are useful in particular in a method of treatment and/or prevention of proliferative diseases, neurodegenerative diseases, and other genomic instability associated diseases.

  本发明提供了结构式（1）所代表的化合物： 其中 R1、R2、R3 和 R4 如权利要求中定义。这些化合物是核酸酶的抑制剂，尤其适用于增殖性疾病、神经退行性疾病和其他基因组不稳定性相关疾病的治疗和/或预防方法。
• Novel synthesis of 2-amino-3-hetaryl-4(5H)-oxothiophenes
  作者：Yu. M. Volovenko、T. A. Volovnenko、A. V. Dobrydnev

  DOI：10.1007/s10593-006-0132-0

  日期：2006.5
• New, simple synthesis of 1-amino(imino)-3-methyl-pyrido[1,2-a]-benzimidazole-4-carbonitriles
  作者：Yu. M. Volovenko、V. V. Ivanov

  DOI：10.1007/bf02253238

  日期：1997.9
• Nucleophilic substitution in a series of 2-methylsulfonyl-5-chloropyrimidine-4-carboxylic acid derivatives
  作者：Yu. M. Volovenko、E. V. Blyumin

  DOI：10.1007/bf02290725

  日期：1998.3