2-[4-(1H-1,2,3,-triazole-1-yl)phenyl]-6-tributylstannylimidazo[1,2-a]pyridine | 1414534-12-5

• 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-[4-(1H-1,2,3,-triazole-1-yl)phenyl]-6-tributylstannylimidazo[1,2-a]pyridine
• 英文别名: 2-[4-(1H-1,2,3-triazol-1-yl)phenyl]-6-tributylstannylimidazo[1,2-a]pyridine；Tributyl-[2-[4-(triazol-1-yl)phenyl]imidazo[1,2-a]pyridin-6-yl]stannane；tributyl-[2-[4-(triazol-1-yl)phenyl]imidazo[1,2-a]pyridin-6-yl]stannane
• CAS: 1414534-12-5
• 化学式: C₂₇H₃₇N₅Sn
• 分子量: 550.334
• InChiKey: JYJHDKLAUYWCKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.64
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[4-(1H-1,2,3,-triazole-1-yl)phenyl]-6-tributylstannylimidazo[1,2-a]pyridine 在 盐酸 、 sodium iodide 、 双氧水 作用下， 以 水 、 乙腈 为溶剂， 反应 0.17h， 生成 ¹²³I-6-iodo-2-[4-(1H-1,2,3,-triazole-1-yl)phenyl]imidazo[1,2-a]pyridine
  参考文献：
  名称：

  RADIOACTIVE IODINE LABELED COMPOUND HAVING AFFINITY FOR AMYLOID

  摘要：

  公开号：

  EP2716641B1
• 作为产物：
  描述：

  4-叠氮苯甲酰甲基溴 在 四(三苯基膦)钯 、 copper(ll) sulfate pentahydrate 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 26.08h， 生成 2-[4-(1H-1,2,3,-triazole-1-yl)phenyl]-6-tributylstannylimidazo[1,2-a]pyridine
  参考文献：
  名称：

  RADIOACTIVE IODINE LABELED COMPOUND HAVING AFFINITY FOR AMYLOID

  摘要：

  公开号：

  EP2716641B1

文献信息

• Design, Synthesis, and Preliminary Evaluation of SPECT Probes for Imaging β-Amyloid in Alzheimer’s Disease Affected Brain
  作者：Yuki Okumura、Yoshifumi Maya、Takako Onishi、Yoshinari Shoyama、Akihiro Izawa、Daisaku Nakamura、Shigeyuki Tanifuji、Akihiro Tanaka、Yasushi Arano、Hiroki Matsumoto

  DOI：10.1021/acschemneuro.8b00064

  日期：2018.6.20

  In this study, we synthesized of a series of 2phenyl- and 2-pyridyl-imidazo[1,2-a]pyridine derivatives and examine their suitability as novel probes for single-photon emission computed tomography (SPECT)-based imaging of beta-amyloid (A beta). Among the 11 evaluated compounds, 10 showed moderate affinity to A beta(1-42) aggregates, exhibiting half-maximal inhibitory concentrations (IC50) of 14.7 +/- 6.07-87.6 +/- 39.8 nM. In vitro autoradiography indicated that 1231 labeled triazole-substituted derivatives displayed highly selective binding to A beta plaques in the hippocampal region of Alzheimer's disease (AD)-affected brain. Moreover, biodistribution studies performed on normal rats demonstrated that all I-123-labeled probes featured high initial uptake into the brain followed by a rapid washout and were thus well suited for imaging A beta plaques, with the highest selectivity observed for a 1H-1,2,3-triazole-substituted 2-pyridyl-imidazopyridine derivative, [I-123]ABC577. This compound showed good kinetics in rat brain as well as moderate in vivo stability in rats and is thus a promising SPECT imaging probe for AD in clinical settings.