4-(2-phenylethyl)-1H-imidazol-2-amine | 1033822-52-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(2-phenylethyl)-1H-imidazol-2-amine
• 英文别名: 5-Phenethyl-1H-imidazol-2-amine；5-(2-phenylethyl)-1H-imidazol-2-amine
• CAS: 1033822-52-4
• 化学式: C₁₁H₁₃N₃
• 分子量: 187.244
• InChiKey: JWSUUOBMJYGKOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  54.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-溴-4-苯基-2-丁酮 在 盐酸 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 4-(2-phenylethyl)-1H-imidazol-2-amine
  参考文献：
  名称：

  Novel 1H-imidazol-2-amine derivatives as potent and orally active vascular adhesion protein-1 (VAP-1) inhibitors for diabetic macular edema treatment

  摘要：

  Novel thiazole derivatives were synthesized and evaluated as vascular adhesion protein-1 (VAP-1) inhibitors. Although we previously identified a compound (2) with potent VAP-1 inhibitory activity in rats, the human activity was relatively weak. Here, to improve the human VAP-1 inhibitory activity of compound 2, we first evaluated the structure-activity relationships of guanidine bioisosteres as simple small molecules and identified a 1H-benzimidazol-2-amine (5) with potent activity compared to phenylguanidine (1). Based on the structure of compound 5, we synthesized a highly potent VAP-1 inhibitor (37b; human IC50 = 0.019 mu M, rat IC50 = 0.0051 mu M). Orally administered compound 37b also markedly inhibited ocular permeability in streptozotocin-induced diabetic rats after oral administration, suggesting it is a promising compound for the treatment of diabetic macular edema. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.04.011

文献信息

• IMIDAZOLE DERIVATIVES
  申请人：Galley Guido

  公开号：US20080146523A1

  公开（公告）日：2008-06-19

  The invention relates to imidazole derivatives which have a good affinity to the trace amine associated receptors (TAARs), especially for TAAR1. The invention also relates to a pharmaceutically-suitable acid-addition salt of the above compound. The invention further relates to a composition comprising an imidazole derivative as described above, or a pharmaceutically-suitable acid-addition salt thereof, and to processes for preparing such compounds.

  这项发明涉及对咪唑衍生物的研究，这些衍生物与微量胺相关受体（TAARs）有很好的亲和力，特别是对于TAAR1。该发明还涉及上述化合物的药用适宜的酸盐。该发明还涉及一种包含上述咪唑衍生物或其药用适宜的酸盐的组合物，以及制备这些化合物的方法。
• Imidazole derivatives
  申请人：Galley Guido

  公开号：US08399463B2

  公开（公告）日：2013-03-19

  The invention relates to imidazole derivatives which have a good affinity to the trace amine associated receptors (TAARs), especially for TAAR1. The invention also relates to a pharmaceutically-suitable acid-addition salt of the above compound. The invention further relates to a composition comprising an imidazole derivative as described above, or a pharmaceutically-suitable acid-addition salt thereof, and to processes for preparing such compounds.

  本发明涉及一种咪唑衍生物，该咪唑衍生物具有良好的亲和力，特别是对于TAAR1（追踪胺相关受体）。本发明还涉及上述化合物的药学适宜的酸加成盐。本发明进一步涉及一种组合物，该组合物包括上述咪唑衍生物或其药学适宜的酸加成盐，并涉及制备这种化合物的过程。
• 4-IMIDAZOLINES AS TAAR'S LIGANDS
  申请人：F. Hoffmann-La Roche AG

  公开号：EP2094668A2

  公开（公告）日：2009-09-02
• US8399463B2
  申请人：——

  公开号：US8399463B2

  公开（公告）日：2013-03-19
• [EN] 4-IMIDAZOLINES AS TAAR'S LIGANDS<br/>[FR] 4-IMIDAZOLINES EN TANT QUE LIGANDS DE TAAR
  申请人：HOFFMANN LA ROCHE

  公开号：WO2008074679A2

  公开（公告）日：2008-06-26

  [EN] The invention relates to compounds of formula (I) wherein R is hydrogen, lower alkyl or amino; X-R¹ is -CH₂ -, -CH(lower alkoxy)- or -CH(OH)- and Y-R² is -CH₂, -CH(lower alkyl)-, -CH(lower alkoxy)- -O-, -S-, -S(O)-, -S(O)₂ -, -CH(phenyl)- or -C(lower alkyl)₂ -; or X-R¹ is -NH- and Y-R² is -CH₂, -CH(lower alkyl)-, -CH(lower alkoxy)-, -CH(phenyl)- or -C(lower alkyl)₂ -; Ar is phenyl, napthyl or benzofuranyl, which rings are unsubstituted or substituted by one or more substituents, selected from the group consisting of lower alkyl, lower alkyl substituted by halogen, halogen, lower alkoxy, lower alkoxy substituted by halogen, hydroxy, amino, di-alkylamino, morpholinyl, phenyl, benzyl or by O-benzyl; or to pharmaceutically suitable acid addition salts. It has been found that the compounds of formula (I) have a good affinity to the trace amine associated receptors (TAARs), especially for TAAR1. The compounds may be used for the treatment of depression, anxiety disorders, bipolar disorder, attention deficit hyperactivity disorder (ADHD), stress-related disorders, psychotic disorders such as schizophrenia, neurological diseases such as Parkinson's disease, neurodegenerative disorders such as Alzheimer's disease, epilepsy, migraine, hypertension, substance abuse and metabolic disorders such as eating disorders, diabetes, diabetic complications, obesity, dyslipidemia, disorders of energy consumption and assimilation, disorders and malfunction of body temperature homeostasis, disorders of sleep and circadian rhythm, and cardiovascular disorders.
  [FR] L'invention porte sur des composés représentés par la formule (I) dans laquelle R est hydrogène, alkyle inférieur ou amino ; X-R¹ est -CH₂-, -CH(alcoxy inférieur)- ou -CH(OH)- et Y-R² est -CH₂, -CH(alkyle inférieur)-, -CH(alcoxy inférieur)-, -O-, -S-, -S(O)-, -S(O)₂-, -CH(phényle)- ou -C(alkyle inférieur)₂-; ou X-R¹ est -NH- et Y-R² est -CH₂, -CH(alkyle inférieur)-, -CH(alcoxy inférieur)-, -CH(phényle)- ou -C(alkyle inférieur)₂-; Ar est phényle, naphtyle or benzofuranyle, ces cycles étant non substitués ou substitués par un ou plusieurs substituants choisis dans le groupe constitué par alkyle inférieur, alkyle inférieur substitué par halogène, halogène, alcoxy inférieur, alcoxy inférieur substitué par halogène, hydroxy, amino, dialkylamino, morpholinyle, phényle, benzyle ou par O-benzyle ; ou sur des sels d'addition avec les acides, pharmaceutiquement appropriés. Il a été trouvé que les composés de formule (I) ont une bonne affinité pour les récepteurs associés aux amines de trace (TAAR), notamment pour TAAR1. Les composés peuvent être utilisés pour le traitement de la dépression, de troubles de l'anxiété, du trouble bipolaire, de l'hyperactivité avec déficit de l'attention (ADHD), de troubles liés au stress, de troubles psychotiques tels que la schizophrénie, de troubles neurologiques tels que la maladie de Parkinson, de troubles neurodégénératifs tels que la maladie d'Alzheimer, de l'épilepsie, de la migraine, de l'hypertension, d'un abus de substances et de troubles métaboliques tels que les troubles de l'alimentation, le diabète, les complications diabétiques, l'obésité, la dyslipidémie, les troubles de la consommation et de l'assimilation de l'énergie, les troubles et le dysfonctionnement de l'homéostasie de la température corporelle, les troubles du sommeil et du rythme circadien et les troubles cardiovasculaires.