4-Chloromethyl-2-(2,3-dimethoxy-phenyl)-1H-imidazole

• 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-Chloromethyl-2-(2,3-dimethoxy-phenyl)-1H-imidazole
• 英文别名: 5-(chloromethyl)-2-(2,3-dimethoxyphenyl)-1H-imidazole
• 化学式: C₁₂H₁₃ClN₂O₂
• 分子量: 252.7
• InChiKey: DJKFHALTPOWDSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  47.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Chloromethyl-2-(2,3-dimethoxy-phenyl)-1H-imidazole 在 氢溴酸 、 sodium ethanolate 作用下， 反应 76.25h， 生成 2-Amino-3-[2-(2,3-dihydroxy-phenyl)-1H-imidazol-4-yl]-propionic acid; hydrobromide
  参考文献：
  名称：

  Synthesis and preliminary evaluation of hydroquinone-substituted histidine derivatives as putative histaminergic neurotoxins

  摘要：

  A series of hydroquinone-substituted histidine derivatives were synthesized as potential histaminergic neurotoxins. The compounds undergo autoxidation at physiologic pH as exemplified by 2-amino-3-[2-4,5,-trihydroxyphenyl)imidazo-4-yl]propionic acid 11. One of the synthesized histidine derivatives, namely 2-amino-3-[2-(2,3-dihydroxyphenyl)imidazo-4-yl]propionic acid 8, was tested for its degenerating effect on histaminergic, dopaminergic and serotonergic neurons in rat brain. After 4 d of an unilateral injection of 1 mu l 3 mM 8 in 0.1 M phosphate buffer (pH 7.4) into the posterior hypothalamus, a decrease in immunoreactivity in the presumable histaminergic neurons was observed whilst dopaminergic and serotonergic neuronal elements were little affected. A possible mechanism of action is discussed.

  DOI：

  10.1016/0223-5234(94)90142-2
• 作为产物：
  描述：

  2-(2,3-dimethoxyphenyl)-4-(hydroxymethyl)imidazole 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 生成 4-Chloromethyl-2-(2,3-dimethoxy-phenyl)-1H-imidazole
  参考文献：
  名称：

  2-（2,3-二甲氧基苯基）-4-（氨基甲基）咪唑类似物的合成及其对多巴胺D（2）和D（3）受体的结合亲和力。

  摘要：

  制备了一系列的2-（2,3-二甲氧基苯基）-4-（氨基甲基）咪唑衍生物，并使用体外结合试验测量了它们对多巴胺D（2）和D（3）受体的亲和力。还制备了几种恶二唑类似物，并测试了它们对多巴胺D（2）和D（3）受体的亲和力。受体结合研究的结果表明，在苯环和碱性氮之间并入咪唑部分并不会显着增加对多巴胺D（3）受体的选择性，而在同一区域并入恶二唑会导致总的两个多巴胺受体亚型结合位点的亲和力丧失。该系列中选择性最高的化合物是2-（5-溴-2,3-二甲氧基苯基）-4-（6,7-二甲氧基-1,2,3,4-四氢异喹啉甲基）咪唑（5i），具有21nM的D（3）受体亲和力，对D（3）与D（2）受体的选择性是7倍。还测量了对sigma（1）和sigma（2）受体的结合亲和力，结果表明几种类似物是选择性的sigma（1）受体配体。

  DOI：

  10.1016/s0968-0896(01)00175-4

文献信息

• 2-Phenyl-4-(aminomethyl)imidazoles as Potential Antipsychotic Agents. Synthesis and Dopamine D2 Receptor Binding
  作者：Andrew Thurkauf、Alan Hutchison、John Peterson、Linda Cornfield、Robin Meade、Kevin Huston、Kristine Harris、Philip C. Ross、Karen Gerber、T. V. Ramabhadran

  DOI：10.1021/jm00012a026

  日期：1995.6

  A series of 2-phenyl-4-(aminomethyl)imidazoles were designed as conformationally restricted analogs of the dopamine D-2 selective benzamide antipsychotics. The title compounds were synthesized and tested for blockade of[H-3]YM-09151 binding in cloned African green monkey dopamine D-2 receptor preparations. The binding affinity data thus obtained were compared against that of the benzamides and a previously described series of 2-phenyl-5-(aminomethyl)-pyrroles.