ethyl 2-(4-pyridyl)-1H-benzimidazole-5-carboxylate

• 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: ethyl 2-(4-pyridyl)-1H-benzimidazole-5-carboxylate
• 英文别名: ethyl 2-pyridin-4-yl-3H-benzimidazole-5-carboxylate
• 化学式: C₁₅H₁₃N₃O₂
• 分子量: 267.287
• InChiKey: QNQJZNBSQQSQNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(4-pyridyl)-1H-benzimidazole-5-carboxylate 在 sodium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 6.0h， 以96%的产率得到2-(pyridin-4-yl)-1H-1,3-benzodiazole-6-carboxylic acid hydrochloride
  参考文献：
  名称：

  新型PDE10A抑制剂-1 H -1,3-苯并二唑和咪唑并[1,2- a ]嘧啶的合成与表征

  摘要：

  含有[1,2,4]三唑[1,5- a ]吡啶（I），吡唑并[1,5- a ]吡啶（II），1 H -1,3-苯并二唑（III）和咪唑[设计并合成了1,2- α ]嘧啶（IV）骨架用于PDE10A相互作用。在这些化合物中，1 H -1,3-苯并二唑和咪唑并[1,2- a ]嘧啶类化合物对PDE10A酶的亲和力最高，且代谢稳定性良好。这两类化合物均被鉴定为选择性和有效的PDE10A酶抑制剂。

  DOI：

  10.1016/j.ejmech.2018.05.043
• 作为产物：
  描述：

  ethyl 4-amino-3-(pyridine-4-carbonyl-amino)benzoate 在 溶剂黄146 作用下， 以58%的产率得到ethyl 2-(4-pyridyl)-1H-benzimidazole-5-carboxylate
  参考文献：
  名称：

  Development of 2-(4-pyridyl)-benzimidazoles as PKN2 chemical tools to probe cancer

  摘要：

  Kinases are signalling proteins which have proven to be successful targets for the treatment of a variety of diseases, predominantly in cancers. However, only a small proportion of kinases ( < 20%) have been investigated for their therapeutic viability, likely due to the lack of available chemical tools across the kinome. In this work we describe initial efforts in the development of a selective chemical tool for protein kinase N2 (PKN2), a relatively unexplored kinase of interest in several types of cancer. The most successful compound, 5, has a measured IC50 of 0.064 mu M against PKN2, with ca. 17-fold selectivity over close homologue, PKN1.

  DOI：

  10.1016/j.bmcl.2020.127040

文献信息

• Benzoimidazole derivatives as anticancer agents
  申请人：CENTRE LEON BERARD

  公开号：US11384081B2

  公开（公告）日：2022-07-12

  The disclosure relates to benzoimidazole derivatives, acting as anticancer drugs, as well as pharmaceutical composition containing said compounds. These compounds are able to firstly inhibit the protein/protein interactions of the MAP Kinase Erk, leading to inhibition of proliferation and secondly to induce apoptosis in human cancer cell lines.

  本公开涉及作为抗癌药物的苯并咪唑衍生物，以及含有上述化合物的药物组合物。这些化合物首先能抑制 MAP 激酶 Erk 的蛋白/蛋白相互作用，从而抑制增殖，其次能诱导人类癌细胞株凋亡。
• BENZOIMIDAZOLE DERIVATIVES AS ANTICANCER AGENTS
  申请人：Centre Leon Berard

  公开号：EP3515904A1

  公开（公告）日：2019-07-31
• Benzoimidazole Derivatives As Anticancer Agents
  申请人：CENTRE LEON BERARD

  公开号：US20220348587A1

  公开（公告）日：2022-11-03

  The disclosure relates to benzoimidazole derivatives, acting as anticancer drugs, as well as pharmaceutical composition containing the compounds. These compounds are able to firstly inhibit the protein/protein interactions of the MAP Kinase Erk, leading to inhibition of proliferation and secondly to induce apoptosis in human cancer cell lines.
• [EN] BENZOIMIDAZOLE DERIVATIVES AS ANTICANCER AGENTS<br/>[FR] DÉRIVÉS DE BENZOIMIDAZOLE EN TANT QU'AGENTS ANTICANCÉREUX
  申请人：CENTRE LEON BERARD

  公开号：WO2018054989A1

  公开（公告）日：2018-03-29

  The invention relates to benzoimidazole derivatives, acting as anticancer drugs, as well as pharmaceutical composition containing said compounds. These compounds are able to firstly inhibit the protein/protein interactions of the MAP Kinase Erk, leading to inhibition of proliferation and secondly to induce apoptosis in human cancer cell lines.
• Synthesis and characterization of novel classes of PDE10A inhibitors - 1H-1,3-benzodiazoles and imidazo[1,2-a]pyrimidines
  作者：Rafał Moszczyński-Pętkowski、Jakub Majer、Małgorzata Borkowska、Łukasz Bojarski、Sylwia Janowska、Mikołaj Matłoka、Filip Stefaniak、Damian Smuga、Katarzyna Bazydło、Krzysztof Dubiel、Maciej Wieczorek

  DOI：10.1016/j.ejmech.2018.05.043

  日期：2018.7

  compounds containing [1,2,4]triazolo [1,5-a]pyridine (I), pyrazolo [1,5-a]pyridine (II), 1H-1,3-benzodiazole (III) and imidazo [1,2-a]pyrimidine (IV) backbones were designed and synthesized for PDE10A interaction. Among these compounds, 1H-1,3-benzodiazoles and imidazo [1,2-a]pyrimidines showed the highest affinity for PDE10A enzyme as well as good metabolic stability. Both classes of compounds were identified

  含有[1,2,4]三唑[1,5- a ]吡啶（I），吡唑并[1,5- a ]吡啶（II），1 H -1,3-苯并二唑（III）和咪唑[设计并合成了1,2- α ]嘧啶（IV）骨架用于PDE10A相互作用。在这些化合物中，1 H -1,3-苯并二唑和咪唑并[1,2- a ]嘧啶类化合物对PDE10A酶的亲和力最高，且代谢稳定性良好。这两类化合物均被鉴定为选择性和有效的PDE10A酶抑制剂。