ethyl 2-(6,8-dichloro-2-phenylimidazo[1,2-a]pyridin-3-yl)acetate | 573704-22-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 2-(6,8-dichloro-2-phenylimidazo[1,2-a]pyridin-3-yl)acetate
• CAS: 573704-22-0
• 化学式: C₁₇H₁₄Cl₂N₂O₂
• 分子量: 349.216
• InChiKey: RJIXPCUFEQDVAR-UHFFFAOYSA-N

物化性质

• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.41
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  43.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-(6,8-dichloro-2-phenylimidazo[1,2-a]pyridin-3-yl)acetate 在 sodium hydroxide 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 4.5h， 生成 N-(ethoxycarbonyl-methyl)(2-phenyl-6,8-dichloro-imidazo[1,2-a]pyridine-3-yl)-acetamide
  参考文献：
  名称：

  Alpidem analogues containing a GABA or glycine moiety as new anticonvulsant agents

  摘要：

  Alpidem analogues containing a GABA (1-3) or glycine (4-6) moiety were synthesized and their interaction with the GABA/benzodiazepine receptor complex at central (CBR) and peripheral (PBR) level was evaluated. In particular, their ability to modulate the specific binding of [H-3]-GABA to washed membrane preparations from the rat cerebral cortex, as well as their effects on human recombinant GABA(A) receptors in Xenopus laevis oocytes, were assessed. Results from these in vitro assays showed that the most active compounds were 1 and 4. Intraperitoneal administration of compound 1 at a dose of 150 mg/kg significantly antagonized pentylenetetrazole-induced seizures in rats and the protective effects were evident for 90 min. However, compound 4 failed to interact with strychnine-sensitive Gly-binding sites. Consistent with these binding results, intraperitoneal administration of compound 4 at 150 mg/kg showed no effect against convulsions induced by strychnine, except for a prolonged time of the latency of convulsions. The results obtained suggest that compound 1 possesses interesting anticonvulsant activity and deserves further investigation as a novel lipophilic GABA derivative. (C) 2003 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0928-0987(03)00002-2
• 作为产物：
  描述：

  4-氧代-4-苯基丁酸乙酯 在 溴 、 溶剂黄146 作用下， 生成 ethyl 2-(6,8-dichloro-2-phenylimidazo[1,2-a]pyridin-3-yl)acetate
  参考文献：
  名称：

  2-苯基咪唑并[1,2-α]吡啶衍生物的合成及其对中心和外围苯并二氮杂receptor受体的结合亲和力。针对外围类型的一系列新的高亲和力和选择性配体。

  摘要：

  若干个6-取代或6,8-二取代的2-苯基咪唑并[1,2-α-吡啶-3-羧酸烷基酯5a-h，-乙酸酯5i-s，6a-g和-丙酸酯5t，6h和N，N-二烷基-2-苯基咪唑并[1,2-α吡啶-3-甲酰胺7a-d，-乙酰胺7e-t或-丙酰胺7u是按照新的合成方法制备的，并且它们对两个环的亲和力（CBR ）和外围（PBR）苯并二氮杂receptor受体进行了评估。酯系列化合物对两种受体类型均显示出低亲和力。相反，大多数N，N-二烷基（2-苯基咪唑并[1,2-α吡啶基-3-基]乙酰胺）7e-t对CBR或PBR具有高亲和性和选择性，这取决于C（C 6）-和/或杂环系统上的C（8）。特别是，6-取代的化合物7f-n的IC50值之比（IC50（CBR）/ IC50（PBR））为0.32（7m）至232（7k），而6,8-二取代的化合物7o-t大于PBR的选择性是CBR的1000倍。检查了几种不同的苯二氮卓类

  DOI：

  10.1021/jm970112+