2-(3-pyridyl)-1H-benzimidazole-4-carboxamide

• 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: 2-(3-pyridyl)-1H-benzimidazole-4-carboxamide
• 英文别名: 2-(pyridin-3-yl)-1H-benzo[d]imidazole-4-carboxamide；2-(pyridin-3-yl)-1H-benzimidazole-4-carboxamide；2-pyridin-3-ylbenzimidazole-4-carboxamide；2-pyridin-3-yl-1H-benzimidazole-4-carboxamide
• 化学式: C₁₃H₁₀N₄O
• 分子量: 238.249
• InChiKey: ACLJKEBNZAPJKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氨基-3-硝基苯甲酰胺 在 sodium dithionite 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 18.5h， 生成 2-(3-pyridyl)-1H-benzimidazole-4-carboxamide
  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

• Inhibitory properties of 2-substituent-1H-benzimidazole-4-carboxamide derivatives against enteroviruses
  作者：Fei Xue、Xianjin Luo、Chenghao Ye、Weidong Ye、Yue Wang

  DOI：10.1016/j.bmc.2011.03.007

  日期：2011.4

  series of novel benzimidazole derivatives were designed, synthesized, and evaluated for their activities against four kinds of enteroviruses, that is, Coxsackie virus A16, B3, B6 and Enterovirus 71 in VERO cells. Strong activities against enterovirus replication and low cytotoxicities were observed in these benzimidazoles generally. The most promising compound was (l)-2-(pyridin-2-yl)-N-(2-(4-nitrophen

  设计，合成了一系列新型苯并咪唑衍生物，并评估了它们对VERO细胞中四种肠道病毒即柯萨奇病毒A16，B3，B6和肠病毒71的活性。通常在这些苯并咪唑中观察到针对肠病毒复制的强活性和低细胞毒性。最有前途的化合物是（l）-2-（吡啶-2-基）-N-（2-（4-硝基苯基）戊基-3-基）-1 H-苯并咪唑-4-羧酰胺（16），其中高抗病毒效力（IC 50  = 1.76μg/ mL）和出色的选择性指数（328）。选择这些化合物作为新型肠病毒抑制剂进行进一步评估。
• A simple and metal-free one-pot synthesis of 2-substituted-1H-4-carboxamide benzimidazole using 3,6-di(pyridin-2-yl)-1,2,4,5-tetrazine(PYTZ) as catalyst
  作者：Li-Jie Zhang、Kang Yang、Chun-Yu Li、Ya-Quan Sun

  DOI：10.1007/s11696-019-00821-x

  日期：2019.11

  In this work, a simple and green method for the convenient synthetic protocol of 2-substituted-1H-4-carboxamide benzimidazole was reported from 2,3-diaminobenzamide and a variety of aldehydes by condensation. The results showed that 2,3-diaminobenzamide and aldehydes could react under visible light irradiation at ambient temperature in the presence of PYTZ and pumping air (or other oxidant) to obtain the desired compound with simple workup. The structures of 20 synthesized compounds were determined by NMR, IR and HRMS (new compound) techniques. The method was efficient, metal free, green, and selective.

  本研究以 2,3-二氨基苯甲酰胺和多种醛为原料，通过缩合反应，报道了一种简便的 2-取代-1H-4-甲酰胺苯并咪唑的绿色合成方法。结果表明，2,3-二氨基苯甲酰胺和醛在可见光照射下，在PYTZ和抽气（或其他氧化剂）存在的环境温度下发生反应，只需简单的操作即可得到所需的化合物。通过核磁共振、红外和 HRMS（新化合物）技术确定了 20 种合成化合物的结构。该方法具有高效、无金属、绿色和选择性强等特点。
• Synthesis and antiviral activity against Coxsackie virus B3 of some novel benzimidazole derivatives
  作者：Jun Cheng、Jiangtao Xie、Xianjin Luo

  DOI：10.1016/j.bmcl.2004.10.087

  日期：2005.1

  Some benzimidazole derivatives were synthesized and evaluated for their antiviral properties. Compounds 20 and 21 showed potent selective activity against Coxsackie virus B-3 in VERO cells. Some structure-activity relationships were discussed. (C) 2004 Elsevier Ltd. All rights reserved.
• US6696437B1
  申请人：——

  公开号：US6696437B1

  公开（公告）日：2004-02-24
• Development of 2-(4-pyridyl)-benzimidazoles as PKN2 chemical tools to probe cancer
  作者：Fiona Scott、Angela M. Fala、Lewis E. Pennicott、Tristan D. Reuillon、Katlin B. Massirer、Jonathan M. Elkins、Simon E. Ward

  DOI：10.1016/j.bmcl.2020.127040

  日期：2020.4

  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.