2-(6-chloro-2-(4-methoxyphenyl)imidazo[1,2-a]pyridin-3-yl)acetic acid | 365213-64-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(6-chloro-2-(4-methoxyphenyl)imidazo[1,2-a]pyridin-3-yl)acetic acid
• 英文别名: 2-(6-Chloro-2-(4-methoxyphenyl)imidazo[1,2-a]pyridin-3-yl)acetic acid；2-[6-chloro-2-(4-methoxyphenyl)imidazo[1,2-a]pyridin-3-yl]acetic acid
• CAS: 365213-64-5
• 化学式: C₁₆H₁₃ClN₂O₃
• 分子量: 316.744
• InChiKey: IHAKNMJBUNAUHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(6-chloro-2-(4-methoxyphenyl)imidazo[1,2-a]pyridin-3-yl)acetic acid 在 氢溴酸 、 三乙胺 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 4-(6-chloro-3-(2-(dipropylamino)-2-oxoethyl)imidazo[1,2-a]pyridin-2-yl)phenyl-3,4-dihydroxyphenethylcarbamate
  参考文献：
  名称：

  Novel codrugs with GABAergic activity for dopamine delivery in the brain

  摘要：

  This study investigates the use of codrugs of the GABAergic agent 2-phenyl-imidazo[1,2-a]pyridinacetamide and dopamine (DA) or ethyl ester L-Dopa (LD) as a strategy to deliver DA and simultaneously activate GABA-receptors in the brain. For this purpose, both DA and LD ethyl ester were linked by carbamate bond to imidazo[1,2-a]pyridine acetamide moieties to yield two DA- and two LD-imidazopyridine derivatives. These compounds were evaluated in vitro to assess their stability, binding affinities and cell membrane transport, and in vivo to assess their bio-availability via microdialysis studies. The two DA derivatives were adequately stable in buffered solution, but underwent cleavage in diluted human serum. By contrast, the LD derivatives were unstable in buffered solution. Receptor binding studies showed that the DA-imidazopyridine carbamates had binding affinity for benzodiazepine receptors in the nanomolar range. Brain microdialysis experiments indicated that intraperitoneal administration of the DA derivatives sustained DA levels in rat striatum over a 4-h period.These results suggest that DA-imidazopyridine carbamates are new DA codrugs with potential application for DA replacement therapy. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ijpharm.2012.08.023
• 作为产物：
  描述：

  2-(6-chloro-2-(4-methoxyphenyl)imidazo[1,2-a]pyridin-3-yl)acetamide 在 水 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以94%的产率得到2-(6-chloro-2-(4-methoxyphenyl)imidazo[1,2-a]pyridin-3-yl)acetic acid
  参考文献：
  名称：

  针对 18-kDa 转运蛋白的新型荧光探针的设计、合成和生物学评价

  摘要：

  来自具有 7-nitro-2-oxa-1,3-diazol-4-yl (NBD) 的 6-chloro-2-phenylimidiazo[1,2- a ]pyridine-3-yl acetamides 配体的一系列荧光探针已合成并对其荧光特性和与 18-kDa 易位蛋白 (TSPO) 的结合亲和力进行了生物学评估。包括 UV/Vis 吸收和荧光测量在内的光谱研究表明，合成的荧光探针表现出良好的光谱特性，尤其是在非极性环境中。体外注射脂多糖 (LPS) 小鼠脑切片的荧光染色显示探针与 TSPO 部分共定位。在[ 11 C]PK11195 放射性配体结合测定中，在从大鼠脑匀浆中分离的粗线粒体级分上测量探针的TSPO结合亲和力。所有新的荧光探针都表现出对 TSPO 的中等至高结合亲和力，亲和力 ( K i ) 值范围为 0.58 nM 至 3.28 μM。综合这些数据，我们建议新的荧光探针可用于可视化

  DOI：

  10.1002/cmdc.202000984

文献信息

• Fluorinated Ligands for Targeting Peripheral Benzodiazepine Receptors
  申请人：Katsifis Andrew

  公开号：US20100209345A1

  公开（公告）日：2010-08-19

  The invention provides fluorinated compounds of formula (I): The compounds may be used in diagnosis or treatment of a disorder in a mammal characterised by an abnormal density of peripheral benzodiazepine receptors.

  该发明提供了化学式（I）的氟化合物：这些化合物可用于诊断或治疗哺乳动物中外周苯二氮平受体密度异常的疾病。
• Lange; Karolak-Wojciechowska; Wejroch, Acta poloniae pharmaceutica, 2001, vol. 58, # 1, p. 43 - 52
  作者：Lange、Karolak-Wojciechowska、Wejroch、Rump

  DOI：——

  日期：——
• Novel codrugs with GABAergic activity for dopamine delivery in the brain
  作者：Nunzio Denora、Tommaso Cassano、Valentino Laquintana、Antonio Lopalco、Adriana Trapani、Concetta Stefania Cimmino、Leonardo Laconca、Andrea Giuffrida、Giuseppe Trapani

  DOI：10.1016/j.ijpharm.2012.08.023

  日期：2012.11

  This study investigates the use of codrugs of the GABAergic agent 2-phenyl-imidazo[1,2-a]pyridinacetamide and dopamine (DA) or ethyl ester L-Dopa (LD) as a strategy to deliver DA and simultaneously activate GABA-receptors in the brain. For this purpose, both DA and LD ethyl ester were linked by carbamate bond to imidazo[1,2-a]pyridine acetamide moieties to yield two DA- and two LD-imidazopyridine derivatives. These compounds were evaluated in vitro to assess their stability, binding affinities and cell membrane transport, and in vivo to assess their bio-availability via microdialysis studies. The two DA derivatives were adequately stable in buffered solution, but underwent cleavage in diluted human serum. By contrast, the LD derivatives were unstable in buffered solution. Receptor binding studies showed that the DA-imidazopyridine carbamates had binding affinity for benzodiazepine receptors in the nanomolar range. Brain microdialysis experiments indicated that intraperitoneal administration of the DA derivatives sustained DA levels in rat striatum over a 4-h period.These results suggest that DA-imidazopyridine carbamates are new DA codrugs with potential application for DA replacement therapy. (C) 2012 Elsevier B.V. All rights reserved.
• Design, Synthesis, and Biological Evaluation of Novel Fluorescent Probes Targeting the 18‐kDa Translocator Protein
  作者：Hendris Wongso、Tomoteru Yamasaki、Katsushi Kumata、Maiko Ono、Makoto Higuchi、Ming‐Rong Zhang、Michael J. Fulham、Andrew Katsifis、Paul A. Keller

  DOI：10.1002/cmdc.202000984

  日期：2021.6.17

  homogenates in a [11C]PK11195 radioligand binding assay. All the new fluorescent probes demonstrated moderate to high binding affinity to the TSPO, with affinity (Ki) values ranging from 0.58 nM to 3.28 μM. Taking these data together, we propose that the new fluorescent probes could be used to visualize the TSPO.

  来自具有 7-nitro-2-oxa-1,3-diazol-4-yl (NBD) 的 6-chloro-2-phenylimidiazo[1,2- a ]pyridine-3-yl acetamides 配体的一系列荧光探针已合成并对其荧光特性和与 18-kDa 易位蛋白 (TSPO) 的结合亲和力进行了生物学评估。包括 UV/Vis 吸收和荧光测量在内的光谱研究表明，合成的荧光探针表现出良好的光谱特性，尤其是在非极性环境中。体外注射脂多糖 (LPS) 小鼠脑切片的荧光染色显示探针与 TSPO 部分共定位。在[ 11 C]PK11195 放射性配体结合测定中，在从大鼠脑匀浆中分离的粗线粒体级分上测量探针的TSPO结合亲和力。所有新的荧光探针都表现出对 TSPO 的中等至高结合亲和力，亲和力 ( K i ) 值范围为 0.58 nM 至 3.28 μM。综合这些数据，我们建议新的荧光探针可用于可视化