2-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carbonitrile | 226702-84-7

• 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: 2-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carbonitrile
• 英文别名: 2-pyridin-2-yl-1H-benzimidazole-5-carbonitrile；2-(pyridin-2-yl)-1H-1,3-benzodiazole-5-carbonitrile；2-pyridin-2-yl-3H-benzimidazole-5-carbonitrile
• CAS: 226702-84-7
• 化学式: C₁₃H₈N₄
• mdl: MFCD22581244
• 分子量: 220.233
• InChiKey: JOPNJLSDCGCEFK-UHFFFAOYSA-N

物化性质

• 熔点：
  216-218 °C
• 沸点：
  506.9±48.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carbonitrile 在 lithium aluminium tetrahydride 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.17h， 生成 4-methyl-N-[[2-(2-pyridyl)-1H-benzimidazol-5-yl]methyl]pyrimidine-5-carboxamide
  参考文献：
  名称：

  [EN] COLLAGEN 1 TRANSLATION INHIBITORS AND METHODS OF USE THEREOF
  [FR] INHIBITEURS DE TRADUCTION DE COLLAGÈNE 1 ET LEURS PROCÉDÉS D'UTILISATION

  摘要：

  本发明涉及新型胶原蛋白1翻译抑制剂，其组成物及制备方法，以及用于治疗纤维化的用途，包括肺部、肝脏、肾脏、心脏和皮肤纤维化、IPF、伤口愈合、瘢痕和牙龈纤维增生、全身性硬化症，以及酒精性和非酒精性脂肪肝（NASH）。

  公开号：

  WO2021154902A1
• 作为产物：
  描述：

  吡啶-2-甲醛 、 3,4-二氨基苯甲腈 以 硝基苯 为溶剂， 以36%的产率得到2-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carbonitrile
  参考文献：
  名称：

  Metal-Mediated Inhibition of Escherichia coli Methionine Aminopeptidase:  Structure−Activity Relationships and Development of a Novel Scoring Function for Metal−Ligand Interactions

  摘要：

  We report the discovery of thiabendazole as a potent inhibitor (K-i = 0.4 mu M) of Escherichia coli methionine aminopeptidase (ecMetAP) and the synthesis and pharmacological evaluation of thiabendazole congeners with activity in the upper nanomolar range. Elucidation of the X-ray structure of ecMetAP in complex with thiabendazole and an unrelated inhibitor that was independently described by another group showed that that both compounds bind to an additional Coll ion at the entrance of the active site. This unexpected finding explains the inactivity of the compounds under in vivo conditions. It also allows us to discuss the structure-activity relationships of this series of compounds in a meaningful way, based upon docking runs with an auxiliary metal ion. We describe a new scoring function for the evaluation of metal-mediated inhibitor binding that, unlike the previously used scoring function implemented in the docking program, allows us to distinguish between active and inactive compounds. Finally, conclusions for the structure-based design of in vivo-active inhibitors of ecMetAP are drawn.

  DOI：

  10.1021/jm050476z

文献信息

• Compounds and compositions as anticoagulants
  申请人：Axys Pharmaceuticals, Inc.

  公开号：US06150379A1

  公开（公告）日：2000-11-21

  The present invention relates to novel biheterocyclic derivatives which are factor Xa inhibitors; the pharmaceutically acceptable salts and N-oxides thereof; their uses as therapeutic agents and the methods of their making.

  本发明涉及一种新的双杂环衍生物，它们是Xa因子抑制剂；其药用盐和N-氧化物；它们作为治疗剂的用途以及其制备方法。
• US6150379A
  申请人：——

  公开号：US6150379A

  公开（公告）日：2000-11-21
• [EN] SUBSTITUTED AMIDINOARYL DERIVATIVES AND THEIR USE AS ANTICOAGULANTS<br/>[FR] DERIVES AMIDINOARYLE SUBSTITUES ET LEUR UTILISATION EN TANT QUE COAGULANTS
  申请人：AXYS PHARMACEUTICALS, INC.

  公开号：WO1999026941A1

  公开（公告）日：1999-06-03

  (EN) The present invention relates to novel biheterocyclic derivatives which are factor Xa inhibitors; the pharmaceutically acceptable salts and $i(N)-oxides thereof; their uses as therapeutic agents and the methods of their making.(FR) La présente invention concerne de nouveaux dérivés bihétérocycliques inhibiteurs du facteur Xa, leurs oxydes de $i(N) et leurs sels pharmaceutiquement acceptables, leurs utilisations en tant qu'agents thérapeutiques et leurs méthodes de production.
• Metal-Mediated Inhibition of <i>Escherichia </i><i>c</i><i>oli</i> Methionine Aminopeptidase:  Structure−Activity Relationships and Development of a Novel Scoring Function for Metal−Ligand Interactions
  作者：Rolf Schiffmann、Alexander Neugebauer、Christian D. Klein

  DOI：10.1021/jm050476z

  日期：2006.1.1

  We report the discovery of thiabendazole as a potent inhibitor (K-i = 0.4 mu M) of Escherichia coli methionine aminopeptidase (ecMetAP) and the synthesis and pharmacological evaluation of thiabendazole congeners with activity in the upper nanomolar range. Elucidation of the X-ray structure of ecMetAP in complex with thiabendazole and an unrelated inhibitor that was independently described by another group showed that that both compounds bind to an additional Coll ion at the entrance of the active site. This unexpected finding explains the inactivity of the compounds under in vivo conditions. It also allows us to discuss the structure-activity relationships of this series of compounds in a meaningful way, based upon docking runs with an auxiliary metal ion. We describe a new scoring function for the evaluation of metal-mediated inhibitor binding that, unlike the previously used scoring function implemented in the docking program, allows us to distinguish between active and inactive compounds. Finally, conclusions for the structure-based design of in vivo-active inhibitors of ecMetAP are drawn.
• [EN] COLLAGEN 1 TRANSLATION INHIBITORS AND METHODS OF USE THEREOF<br/>[FR] INHIBITEURS DE TRADUCTION DE COLLAGÈNE 1 ET LEURS PROCÉDÉS D'UTILISATION
  申请人：ANIMA BIOTECH INC

  公开号：WO2021154902A1

  公开（公告）日：2021-08-05

  The present invention relates to novel Collagen 1 translation inhibitors, composition and methods of preparation thereof, and uses thereof for treating Fibrosis including lung, liver, kidney, cardiac and dermal fibrosis, IPF, wound healing, scarring and Gingival fibromatosis, Systemic Sclerosis, and alcoholic and non-alcoholic steatohepatitis (NASH).

  本发明涉及新型胶原蛋白1翻译抑制剂，其组成物及制备方法，以及用于治疗纤维化的用途，包括肺部、肝脏、肾脏、心脏和皮肤纤维化、IPF、伤口愈合、瘢痕和牙龈纤维增生、全身性硬化症，以及酒精性和非酒精性脂肪肝（NASH）。