1-[2-(diethylamino)ethyl]-2-(4-ethoxybenzyl)-1H-benzo[d]imidazol-5-amine | 75821-80-6

• 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-[2-(diethylamino)ethyl]-2-(4-ethoxybenzyl)-1H-benzo[d]imidazol-5-amine
• 英文别名: 1-(2-diethylamino-ethyl)-2-(4-ethoxy-benzyl)-1H-benzoimidazol-5-ylamine；1-(2-Diethylamino-ethyl)-2-(4-ethoxy-benzyl)-1H-benzoimidazol-5-ylamine；1-[2-(Diethylamino)ethyl]-2-[(4-ethoxyphenyl)methyl]benzimidazol-5-amine
• CAS: 75821-80-6
• 化学式: C₂₂H₃₀N₄O
• 分子量: 366.506
• InChiKey: AWYRKIIHWPBDAA-UHFFFAOYSA-N

物化性质

• 沸点：
  572.2±45.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  56.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[2-(diethylamino)ethyl]-2-(4-ethoxybenzyl)-1H-benzo[d]imidazol-5-amine 在 盐酸 、 sodium azide 、 sodium carbonate 、 三氟乙酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 1.0h， 生成 azidoetonitazene
  参考文献：
  名称：

  Photoactivatable opiate derivatives as irreversible probes of the .mu.-opioid receptor

  摘要：

  The synthesis of aryldiazonium and arylazido derivatives of carfentanil, etonitazene, and naltrexone and of a triazaspirodecane derivative is described. The chemical stability and the spectral characteristics of these compounds were verified, and their binding affinity constants for the different opioid receptor classes were determined, in the absence of light, from competition experiments. With the exception of the naltrexyl derivatives, which remained nonselective, all compounds tested displayed a pronounced mu-binding selectivity with mu/delta and mu/kappa ratios ranging from 12 to 1000. After irradiation, only the arylazido probes led to an irreversible mu-binding-site inactivation. This inactivation fulfilled the criteria for photoaffinity labeling such as protection against inactivation by other opiate ligands and absence of an effect of scavengers on the extent of the inactivation. Most of the photoactivatable probes formed long-lasting reversible complexes with the opioid binding sites: an efficient dissociation procedure was thus required to discriminate between pseudoirreversible and covalent complexes. The marked differences in labeling efficacy between aryldiazonium salts and their corresponding arylazido derivatives are discussed.

  DOI：

  10.1021/jm00171a020
• 作为产物：
  描述：

  N(1)-(2-(二乙基氨基)乙基)-4-硝基苯-1,2-二胺 在 盐酸 、 五氯化磷 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 tin(ll) chloride 作用下， 以 乙醇 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 52.0h， 生成 1-[2-(diethylamino)ethyl]-2-(4-ethoxybenzyl)-1H-benzo[d]imidazol-5-amine
  参考文献：
  名称：

  Synthesis and Molecular Docking for Antiinflammatory Studies of 2-(Arylmethyl)-1-ethyl-1H-benzo[d]imidazol-5-amines

  摘要：

  1-氯-2,4-二硝基苯（1）与脂肪胺（2）在乙醇溶剂中反应，回流条件下反应16-24小时，形成N-烷基-2,4-二硝基苯胺（3）。化合物3经过还原反应生成N-烷基-4-硝基苯-1,2-二胺（4）。化合物4与羧酸（5）反应生成N-(2-(烷基氨基)-5-硝基苯基)-2-芳基乙酰胺（6），该化合物经过环化得到2-(芳基甲基)-1-乙基-5-硝基-1H-苯并[德]咪唑（7）。最后，化合物7经过还原反应生成2-(芳基甲基)-1-乙基-1H-苯并[德]咪唑-5-胺（8）。合成的化合物通过光谱分析进行了表征。合成的化合物得到了光谱分析的确认。使用对接服务器对5COX与配体进行分子对接，预测该化合物为潜在的抗炎化合物。

  DOI：

  10.14233/ajchem.2018.20784

文献信息

• Substituted benzimidazole compounds with dual NOS inhibitory activity and mu opioid agonist activity
  申请人：Renton Paul

  公开号：US20080214613A1

  公开（公告）日：2008-09-04

  The present invention relates to benzimidazole compounds having dual nitric oxide synthase (NOS) inhibitory activity and agonist activity at the mu-opioid receptor, to pharmaceutical and diagnostic compositions containing them, and to their medical use, particularly as compounds for the treatment or prevention of chronic pain, acute pain, migraine, and neuropathic pain.

  本发明涉及具有双重一氧化氮合酶（NOS）抑制活性和μ-阿片受体激动活性的苯并咪唑化合物，以及包含它们的药物和诊断组合物，以及它们的医学用途，特别是作为治疗或预防慢性疼痛、急性疼痛、偏头痛和神经病性疼痛的化合物。
• NOpiates: Novel Dual Action Neuronal Nitric Oxide Synthase Inhibitors with μ-Opioid Agonist Activity
  作者：Paul Renton、Brenda Green、Shawn Maddaford、Suman Rakhit、John S. Andrews

  DOI：10.1021/ml200268w

  日期：2012.3.8

  A novel series of benzimidazole designed multiple ligands (DMLs) with activity at the neuronal nitric oxide synthase (nNOS) enzyme and the mu-opioid receptor was developed. Targeting of the structurally dissimilar heme-containing enzyme and the mu-opioid GPCR was predicated on the modulatory role of nitric oxide on mu-opioid receptor function. Structure activity relationship studies yielded lead compound 24 with excellent nNOS inhibitory activity (IC50 = 0.44 mu M), selectivity over both endothelial nitric oxide synthase (10-fold) and inducible nitric oxide synthase (125-fold), and potent mu-opioid binding affinity, K-i = 5.4 nM. The functional activity as measured in the cyclic adenosine monosphospate secondary messenger assay resulted in full agonist activity (EC50 = 0.34 mu M). This work represents a novel approach in the development of new analgesics for the treatment of pain.
• SUBSTITUTED BENZIMIDAZOLE COMPOUNDS WITH DUAL NOS INHIBITORY ACTIVITY AND MUOPIOID AGONIST ACTIVITY
  申请人：Neuraxon Inc.

  公开号：EP1888568A2

  公开（公告）日：2008-02-20
• EP1888568A4
  申请人：——

  公开号：EP1888568A4

  公开（公告）日：2009-08-12
• US7919510B2
  申请人：——

  公开号：US7919510B2

  公开（公告）日：2011-04-05