2-(4-phenoxyphenyl)-1H-benzo[d]imidazole | 68321-04-0

• 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-(4-phenoxyphenyl)-1H-benzo[d]imidazole
• 英文别名: 2-(4-phenoxyphenyl)benzimidazole；2-(4-phenoxyphenyl)-1H-benzimidazole
• CAS: 68321-04-0
• 化学式: C₁₉H₁₄N₂O
• 分子量: 286.333
• InChiKey: UAQIXVCCXZGITI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-[4-(3-acetylaminophenyl)piperidin-1-yl]propyl methanesulfonate 、 2-(4-phenoxyphenyl)-1H-benzo[d]imidazole 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以95 mg的产率得到2-(4-phenoxyphenyl)-1-{3-[4-(3-acetylaminophenyl)piperidin-1-yl]propyl}-1H-benzimidazole
  参考文献：
  名称：

  Synthesis and SAR investigations of novel 2-arylbenzimidazole derivatives as melanin-concentrating hormone receptor 1 (MCH-R1) antagonists

  摘要：

  Compounds containing 2-arybenzimidazole ring systems linked to arylpiperidines were synthesized and evaluated as MCH-R1 antagonists. The results of structure-activity relationship studies led to the identification of compound 4c as a potent MCH-R1 antagonist (IC50 = 1 nM). This compound also has good metabolic stability, and favorable pharmacokinetic and brain penetration properties. However 4c was found to be potent inhibitor of the hERG potassium channel. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.099
• 作为产物：
  描述：

  4-苯氧基苯甲酸 、 邻苯二胺 在 polyphosphoric acid 作用下， 反应 4.0h， 生成 2-(4-phenoxyphenyl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  Synthesis and SAR investigations of novel 2-arylbenzimidazole derivatives as melanin-concentrating hormone receptor 1 (MCH-R1) antagonists

  摘要：

  Compounds containing 2-arybenzimidazole ring systems linked to arylpiperidines were synthesized and evaluated as MCH-R1 antagonists. The results of structure-activity relationship studies led to the identification of compound 4c as a potent MCH-R1 antagonist (IC50 = 1 nM). This compound also has good metabolic stability, and favorable pharmacokinetic and brain penetration properties. However 4c was found to be potent inhibitor of the hERG potassium channel. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.099

文献信息

• Photochemical Synthesis of Benzimidazoles from Diamines and Aldehydes
  作者：Elpida Skolia、Mary K. Apostolopoulou、Nikolaos F. Nikitas、Christoforos G. Kokotos

  DOI：10.1002/ejoc.202001357

  日期：2021.1.22

  A green, facile, mild, and metal‐free protocol for the synthesis of benzimidazoles by cyclization of diamines and aldehydes was developed, using cheap household lamps as the light source and an organic molecule as the photoinitiator.

  通过廉价的家用灯作为光源，有机分子作为光引发剂，开发了一种绿色，轻便，温和且不含金属的方案，用于通过二胺和醛的环化反应合成苯并咪唑。
• IMIDAZOLE DERIVATIVES HAVING ARYL PIPERIDINE SUBSTITUENT, METHOD FOR PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME
  申请人：Suh Jee Hee

  公开号：US20100145054A1

  公开（公告）日：2010-06-10

  The present invention is directed to a novel imidazole derivative having an aryl piperidine substituent of formula (I) and a method for preparation thereof, and a pharmaceutical composition containing said imidazole derivative as an active ingredient for preventing or treating a MCH (melanine-concentrating hormone)-related disease.

  本发明涉及一种具有式(I)的芳基哌啶取代基的新型咪唑衍生物及其制备方法，以及含有该咪唑衍生物作为活性成分的药物组合物，用于预防或治疗与MCH（黑色素浓集激素）相关的疾病。
• 2-arylbenzimidazoles as PPARGC1A activators for treating neurodegenerative diseases
  申请人：The Board of Trustees of the Leland Stanford Junior University

  公开号：US10851066B2

  公开（公告）日：2020-12-01

  The compound 2-(3-tert-Butylphenyl)-4,6-difluoro-1H-benzo[d]imidazole and its use are disclosed: The compound activates Ppargc1a and, as a consequence, is useful for treating neuroinflammation and for treating a variety of neurodegenerative diseases.

  公开了化合物 2-(3-叔丁基苯基)-4,6-二氟-1H-苯并[d]咪唑及其用途： 该化合物可激活 Ppargc1a，因此可用于治疗神经炎症和各种神经退行性疾病。
• 2-arylbenzimidazoles as Ppargc1a activators for treating neurodegenerative diseases
  申请人：The Board of Trustees of the Leland Stanford Junior University

  公开号：US11111217B2

  公开（公告）日：2021-09-07

  The compound 2-(4-tert-Butylphenyl)-1H-benzo[d]imidazol-5-ol: and its use are disclosed. The compound activates Ppargc1a and, as a consequence, is useful for treating neuroinflammation and for treating a variety of neurodegenerative diseases.

  化合物 2-(4-叔丁基苯基)-1H-苯并[d]咪唑-5-醇： 及其用途。该化合物能激活 Ppargc1a，因此可用于治疗神经炎症和各种神经退行性疾病。
• 2-ARYLBENZIMIDAZOLES AS PPARGC1A ACTIVATORS FOR TREATING NEURODEGENERATIVE DISEASES
  申请人：The Board of Trustees of the Leland Stanford Junior University

  公开号：US20200299244A1

  公开（公告）日：2020-09-24

  The compound 2-(3-tert-Butylphenyl)-4,6-difluoro-1H-benzo[d]imidazole and its use are disclosed: The compound activates Ppargc1a and, as a consequence, is useful for treating neuroinflammation and for treating a variety of neurodegenerative diseases.