5-{4-[6-(tributylstannyl)imidazo[1,2-a]pyridin-2-yl]phenyl}-1,3-oxazole | 938461-45-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 5-{4-[6-(tributylstannyl)imidazo[1,2-a]pyridin-2-yl]phenyl}-1,3-oxazole
• 英文别名: DRM015；5-{4-[6-(1,1,1-tributylstannyl)imidazo[1,2-a]pyridin-2-yl]phenyl}-1,3-oxazole；Tributyl-[2-[4-(1,3-oxazol-5-yl)phenyl]imidazo[1,2-a]pyridin-6-yl]stannane
• CAS: 938461-45-1
• 化学式: C₂₈H₃₇N₃OSn
• 分子量: 550.331
• InChiKey: GCCNZDXSBQMAHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.71
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  43.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-{4-[6-(tributylstannyl)imidazo[1,2-a]pyridin-2-yl]phenyl}-1,3-oxazole 在 sodium iodide 、 chloroamine-T 作用下， 以 aq. phosphate buffer 为溶剂， 生成 5-[4-(6-[¹²⁵I]-iodoimidazo[1,2-a]pyridine-2-yl)phenyl]-1,3-oxazole
  参考文献：
  名称：

  Synthesis and biological evaluation of novel radioiodinated imidazopyridine derivatives for amyloid-β imaging in Alzheimer’s disease

  摘要：

  Non-invasive detection for amyloid-beta peptide (A beta) deposition has important significance for the early diagnosis and medical intervention for Alzheimer's disease (AD). In this study, we developed a series of imidazopyridine derivatives as potential imaging agents for single-photon emission computed tomography (SPECT). Two of them, compounds DRK092 and DRM106, showed higher affinity for synthetic human A beta 1-40 fibrils than did the well-known amyloid-imaging agent IMPY. A metabolite analysis revealed brain-permeable radioactive metabolites of I-125-labeled DRK092 and IMPY; no radioactive metabolites from I-125-labeled DRM106 ([I-125]DRM106) were detected. In addition, in vitro autoradiography clearly demonstrated specific binding of [I-125]DRM106 in the hippocampal region of AD enriched with A beta plaques. Thus, our results strongly suggested that compound DRM106 can be used as an imaging agent for SPECT to detect A beta deposition in AD brain. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.05.043
• 作为产物：
  描述：

  2-溴-4'-氰基苯乙酮 在 四(三苯基膦)钯 、 二异丁基氢化铝 、 碳酸氢钠 、 potassium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 47.25h， 生成 5-{4-[6-(tributylstannyl)imidazo[1,2-a]pyridin-2-yl]phenyl}-1,3-oxazole
  参考文献：
  名称：

  Synthesis and biological evaluation of novel radioiodinated imidazopyridine derivatives for amyloid-β imaging in Alzheimer’s disease

  摘要：

  Non-invasive detection for amyloid-beta peptide (A beta) deposition has important significance for the early diagnosis and medical intervention for Alzheimer's disease (AD). In this study, we developed a series of imidazopyridine derivatives as potential imaging agents for single-photon emission computed tomography (SPECT). Two of them, compounds DRK092 and DRM106, showed higher affinity for synthetic human A beta 1-40 fibrils than did the well-known amyloid-imaging agent IMPY. A metabolite analysis revealed brain-permeable radioactive metabolites of I-125-labeled DRK092 and IMPY; no radioactive metabolites from I-125-labeled DRM106 ([I-125]DRM106) were detected. In addition, in vitro autoradiography clearly demonstrated specific binding of [I-125]DRM106 in the hippocampal region of AD enriched with A beta plaques. Thus, our results strongly suggested that compound DRM106 can be used as an imaging agent for SPECT to detect A beta deposition in AD brain. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.05.043

文献信息

• DIAGNOSTIC AND REMEDY FOR DISEASE CAUSED BY AMYLOID AGGREGATION AND/OR DEPOSITION
  申请人：Fujifilm RI Pharma Co., Ltd.

  公开号：EP1956013B1

  公开（公告）日：2016-04-13