2-[(4-t-butyl-2,6-dimethylphenyl)methyl]-1H-imidazole

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[(4-t-butyl-2,6-dimethylphenyl)methyl]-1H-imidazole
• 英文别名: Xylometazoline metabolite；2-[(4-tert-butyl-2,6-dimethylphenyl)methyl]-1H-imidazole
• 化学式: C₁₆H₂₂N₂
• 分子量: 242.364
• InChiKey: CNOOVUYXUJVGIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  溴甲苯 、 2-[(4-t-butyl-2,6-dimethylphenyl)methyl]-1H-imidazole 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以60%的产率得到2-[(4-t-butyl-2,6-dimethylphenyl)methyl]-1-benzylimidazole
  参考文献：
  名称：

  Imidazoline-modified benzylimidazolines as h5-HT1D/1B serotonergic ligands

  摘要：

  Sumatriptan, a h5-HT1D and h5-HT1B receptor agonist used clinically as a migraine-abortive, produces certain side effects thought to result from its affinity for h(5)-HT1B receptors. The present investigation extends our work with benzylimidazolines as novel non-tryptamine h5-(HT1D/1B) ligands. The effect of N-methylation, N-benzylation, ring-aromatization, and variation of the imidazoline ring on affinity both at h5-HT1D and h5-HT1B receptors was examined. Several compounds were identified with good affinity and enhanced(i.e., > 100-fold) h5-HT1D versus h5-HT1B selectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00275-3
• 作为产物：
  描述：

  赛洛唑啉 在 palladium on activated charcoal 作用下， 以 甲苯 为溶剂， 反应 72.0h， 以66%的产率得到2-[(4-t-butyl-2,6-dimethylphenyl)methyl]-1H-imidazole
  参考文献：
  名称：

  Imidazoline-modified benzylimidazolines as h5-HT1D/1B serotonergic ligands

  摘要：

  Sumatriptan, a h5-HT1D and h5-HT1B receptor agonist used clinically as a migraine-abortive, produces certain side effects thought to result from its affinity for h(5)-HT1B receptors. The present investigation extends our work with benzylimidazolines as novel non-tryptamine h5-(HT1D/1B) ligands. The effect of N-methylation, N-benzylation, ring-aromatization, and variation of the imidazoline ring on affinity both at h5-HT1D and h5-HT1B receptors was examined. Several compounds were identified with good affinity and enhanced(i.e., > 100-fold) h5-HT1D versus h5-HT1B selectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00275-3

文献信息

• Imidazoles with serotonin receptor binding activity
  申请人：Virginia Commonwealth University

  公开号：US06124338A1

  公开（公告）日：2000-09-26

  This invention relates compounds having serotonin receptor binding activity, to pharmaceutical compositions containing them and to their medical use, particularly in the treatment of CNS conditions. Described herein are compounds which have the general formula: ##STR1## wherein R.sup.1 is selected from H, C.sub.1-6 alkyl and benzyl; R.sup.2 is selected from H and C.sub.1-6 alkyl; R.sup.3 is selected from H and C.sub.1-6 alkyl; R.sup.4 is selected from C.sub.1-6 alkyl and halo; R.sup.5 is selected from H and OH; and salts, hydrates and solvates thereof. Also described is the use of these compounds as pharmaceuticals to treat indications where stimulation of subtypes of the serotonin receptor is implicated, such as migraine.

  本发明涉及具有5-羟色胺受体结合活性的化合物，包含它们的制药组合物以及它们在医学上的应用，特别是在中枢神经系统疾病的治疗中。本文所述的化合物具有以下通式：##STR1## 其中R.sup.1选择H、C.sub.1-6烷基和苄基；R.sup.2选择H和C.sub.1-6烷基；R.sup.3选择H和C.sub.1-6烷基；R.sup.4选择C.sub.1-6烷基和卤素；R.sup.5选择H和OH；以及其盐、水合物和溶剂化物。还描述了这些化合物作为药物用于治疗刺激5-羟色胺受体亚型的适应症，例如偏头痛。
• [EN] IMIDAZOLES WITH SEROTONIN RECEPTOR BINDING ACTIVITY<br/>[FR] IMIDAZOLES A ACTIVITE DE FIXATION DU RECEPTEUR DE LA SEROTONINE
  申请人：ALLELIX BIOPHARMACEUTICALS INC.

  公开号：WO1998012183A1

  公开（公告）日：1998-03-26

  (EN) This invention relates to compounds having serotonin receptor binding activity, to pharmaceutical compositions containing them and to their medical use, particularly in the treatment of CNS conditions. Described herein are compounds which have general formula (I), wherein R1 is selected from H, C1-6alkyl and benzyl; R2 is selected from H and C1-6alkyl; R3 is selected from H and C1-6alkyl; R4 is selected from C1-6alkyl and halo; R5 is selected from H and OH; and salts, hydrates and solvates thereof. Also described is the use of these compounds as pharmaceuticals to treat indications where stimulation of subtypes of the serotonin receptor is implicated, such as migraine.(FR) L'invention porte sur des composés présentant une activité de fixation du récepteur de la sérotonine, sur des préparations pharmaceutiques les contenant et sur leurs utilisations médicales notamment pour le traitement des troubles du SNC, ainsi que sur leurs sels, hydrates et solvates. Lesdits composés répondent à la formule générale (I) dans laquelle: R1 est sélectionné parmi H, C1-6 alkyle et benzyle; R2 est sélectionné parmi H et C1-6 alkyle; R3 est sélectionné parmi H et C1-6 alkyle; R4 est sélectionné parmi C1-6 alkyle et halo; R5 est sélectionné parmi H et OH. L'invention porte également sur l'utilisation de ces composés comme produits pharmaceutiques pour traiter les cas où la stimulation des sous-types du récepteur de la sérotonine est en cause, tels que la migraine.

  本发明涉及具有5-羟色胺受体结合活性的化合物，包含它们的药物组成物以及它们在治疗中枢神经系统疾病方面的医学用途。本文描述了通式（I）的化合物，其中R1选自H、C1-6烷基和苄基；R2选自H和C1-6烷基；R3选自H和C1-6烷基；R4选自C1-6烷基和卤素；R5选自H和OH；以及它们的盐、水合物和溶剂化物。还描述了将这些化合物用作药物，以治疗与5-羟色胺受体亚型刺激有关的症状，例如偏头痛。
• US6124338A
  申请人：——

  公开号：US6124338A

  公开（公告）日：2000-09-26
• US6288101B1
  申请人：——

  公开号：US6288101B1

  公开（公告）日：2001-09-11
• Imidazoline-modified benzylimidazolines as h5-HT1D/1B serotonergic ligands
  作者：Thomas Prisinzano、Ho Law、Małgorzata Dukat、Abdelmalik Slassi、Neil MaClean、Lidia Demchyshyn、Richard A. Glennon

  DOI：10.1016/s0968-0896(00)00275-3

  日期：2001.3

  Sumatriptan, a h5-HT1D and h5-HT1B receptor agonist used clinically as a migraine-abortive, produces certain side effects thought to result from its affinity for h(5)-HT1B receptors. The present investigation extends our work with benzylimidazolines as novel non-tryptamine h5-(HT1D/1B) ligands. The effect of N-methylation, N-benzylation, ring-aromatization, and variation of the imidazoline ring on affinity both at h5-HT1D and h5-HT1B receptors was examined. Several compounds were identified with good affinity and enhanced(i.e., > 100-fold) h5-HT1D versus h5-HT1B selectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.