2-(6-Chloro-2-(4-hydroxyphenyl)imidazo[1,2-a]pyridin-3-yl)acetic acid | 1009080-17-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(6-Chloro-2-(4-hydroxyphenyl)imidazo[1,2-a]pyridin-3-yl)acetic acid
• 英文别名: 2-[6-chloro-2-(4-hydroxyphenyl)imidazo[1,2-a]pyridin-3-yl]acetic acid
• CAS: 1009080-17-4
• 化学式: C₁₅H₁₁ClN₂O₃
• 分子量: 302.717
• InChiKey: SOQLIYLLOSLCGP-UHFFFAOYSA-N

物化性质

• 熔点：
  260 °C (decomp)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  74.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(6-Chloro-2-(4-hydroxyphenyl)imidazo[1,2-a]pyridin-3-yl)acetic acid 在 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-氨基-5-氯吡啶 在 水 、 氢溴酸 、 sodium hydroxide 作用下， 以 正丁醇 为溶剂， 生成 2-(6-Chloro-2-(4-hydroxyphenyl)imidazo[1,2-a]pyridin-3-yl)acetic acid
  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

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.

  该发明提供了公式（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。
• Fluorinated ligands for targeting peripheral benzodiazepine receptors
  申请人：AUSTRALIAN NUCLEAR SCIENCE & TECHNOLOGY ORGANISATION

  公开号：EP2752415A1

  公开（公告）日：2014-07-09

  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.

  本发明提供了式 (I) 的含氟化合物： 这些化合物可用于诊断或治疗以外周苯并二氮杂卓受体密度异常为特征的哺乳动物疾病。
• FLUORINATED LIGANDS FOR TARGETING PERIPHERAL BENZODIAZEPINE RECEPTORS
  申请人：AUSTRALIAN NUCLEAR SCIENCE & TECHNOLOGY ORGANISATION

  公开号：EP2054060A1

  公开（公告）日：2009-05-06
• [EN] FLUORINATED LIGANDS FOR TARGETING PERIPHERAL BENZODIAZEPINE RECEPTORS<br/>[FR] LIGANDS FLUORÉS POUR LE CIBLAGE DES RÉCEPTEURS PÉRIPHERIQUES DES BENZODIAZÉPINES
  申请人：AUSTRALIAN NUCLEAR SCIENCE TEC

  公开号：WO2008022396A1

  公开（公告）日：2008-02-28

  [EN] 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.
  [FR] L'invention concerne les composés fluorés de la formule (I) : Les composés peuvent être utilisés dans le cadre du diagnostic ou du traitement d'un trouble survenant chez un mammifère et caractérisé par une anomalie de la densité des récepteurs périphériques aux benzodiazépines.