2-(4-hydroxyphenyl)-6-iodoimidazo[1,2-a]pyridine | 956499-76-6

• 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-hydroxyphenyl)-6-iodoimidazo[1,2-a]pyridine
• 英文别名: 2-(4'-Hydroxyphenyl)-6-iodoimidazo[1,2-a]pyridine；4-(6-iodoimidazo[1,2-a]pyridin-2-yl)phenol
• CAS: 956499-76-6
• 化学式: C₁₃H₉IN₂O
• 分子量: 336.132
• InChiKey: YBOCOHMLQZAQQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-hydroxyphenyl)-6-iodoimidazo[1,2-a]pyridine 在 四(三苯基膦)钯 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 正己烷 为溶剂， 反应 46.0h， 生成 2-(4′-methoxyphenyl)-6-tributylstannylimidazo[1,2-a]pyridine
  参考文献：
  名称：

  Design, Synthesis, and Preliminary Evaluation of SPECT Probes for Imaging β-Amyloid in Alzheimer’s Disease Affected Brain

  摘要：

  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.

  DOI：

  10.1021/acschemneuro.8b00064
• 作为产物：
  描述：

  2-氨基-5-碘吡啶 、 2-溴-4'-羟基苯乙酮 在 乙腈 、 碳酸氢钠 、 水 作用下， 以 乙腈 为溶剂， 反应 5.08h， 以to obtain 526 mg (corresponding to 1.56 mmol) of 2-(4′-hydroxyphenyl)-6-iodoimidazo[1,2-a]pyridine (FIG. 1-7, Step 2)的产率得到2-(4-hydroxyphenyl)-6-iodoimidazo[1,2-a]pyridine
  参考文献：
  名称：

  USE OF NOVEL COMPOUND HAVING AFFINITY FOR AMYLOID, AND PROCESS FOR PRODUCTION OF THE SAME

  摘要：

  本发明提供了一种检测生物组织中淀粉样物质的试剂，该试剂使用与淀粉样物质亲和力强且毒性低（如突变原性）的化合物，可以高灵敏度地在体内外检测淀粉样物质。检测生物组织中沉积的淀粉样物质的试剂包括下式（1）所表示的化合物或其盐：其中，A1、A2、A3和A4独立表示碳或氮，R3是下式所表示的基团：其中，R1是放射性卤素取代基；m为0到4的整数；n为0或1的整数，但至少有一个A1、A2、A3和A4表示碳，并且R3与A1、A2、A3或A4表示的碳结合。

  公开号：

  US20100249408A1

文献信息

• Novel Compound Having Affinity for Amyloid
  申请人：Tanifuji Shigeyuki

  公开号：US20090252679A1

  公开（公告）日：2009-10-08

  The present invention provides a compound which has affinity with amyloid, shows sufficiently rapid clearance from normal tissues and is suppressed in toxicity such as mutagencity. Provided is a compound represented by the following formula (1) or a salt thereof: wherein A 1 , A 2 , A 3 and A 4 independently represents a carbon or nitrogen; R 1 is a halogen substituent; R 2 is a halogen substituent; and m is an integer of 0 to 2, provided that at least one of R 1 and R 2 is a radioactive halogen substituent, at least one of A 1 , A 2 , A 3 and A 4 represents a carbon, and R 1 binds to a carbon represented by A 1 , A 2 , A 3 or A 4 as well as a low-toxic diagnostic agent comprising a compound represented by the preceding formula or a salt thereof.

  本发明提供了一种与淀粉样蛋白亲和力强，从正常组织中清除速度足够快且毒性（如诱变性）被抑制的化合物。所提供的化合物由以下公式（1）或其盐所表示：其中，A1、A2、A3和A4独立地表示碳或氮；R1是卤素取代基；R2是卤素取代基；m是0到2的整数，但至少其中一个R1和R2是放射性卤素取代基，至少一个A1、A2、A3和A4表示碳，且R1与由A1、A2、A3或A4表示的碳结合，以及包含由上述公式或其盐所表示的低毒性诊断剂。
• NOVEL COMPOUND WITH AFFINITY FOR AMYLOID
  申请人：Tanifuji Shigeyuki

  公开号：US20090252680A1

  公开（公告）日：2009-10-08

  A compound represented by the following formula or a salt thereof: wherein each of A 1 , A 2 , A 3 and A 4 independently represents a carbon or nitrogen; R 1 is a group selected from the group consisting of hydrogen, hydroxyl group, carboxyl group, sulfuric acid group, amino group, nitro group, cyano group, non-radioactive halogen substituents, alkyl substituents with 1-4 carbon atoms and alkoxy substituents with 1-4 carbon atoms; and R 2 is a radioactive halogen substituent, provided at least one of A 1 , A 2 , A 3 and A 4 represents a carbon, and R1 binds to a carbon represented by A 1 , A 2 , A 3 or A 4 , is effective as an image diagnosis probe targeting amyloid and as well as a diagnostic agent for Alzheimer's disease including the compound represented by the above formula or a salt thereof.

  以下化合物或其盐所代表的化合物： 其中A1，A2，A3和A4各自独立地代表碳或氮；R1是从氢，羟基，羧基，硫酸基，氨基，硝基，氰基，非放射性卤素取代基，1-4个碳原子的烷基取代基和1-4个碳原子的烷氧基取代基的群中选择的基团；而R2是放射性卤素取代基，前提是A1，A2，A3和A4中至少有一个代表碳，并且R1与A1，A2，A3或A4代表的碳结合，该化合物或其盐的有效成分作为靶向淀粉样蛋白的影像诊断探针以及阿尔茨海默病的诊断剂。
• NOVEL COMPOUND HAVING AFFINITY FOR AMYLOID
  申请人：Tanifuji Shigeyuki

  公开号：US20100069640A1

  公开（公告）日：2010-03-18

  A compound represented by the following formula or a salt thereof: wherein each of A 1 , A 2 , A 3 and A 4 independently represents a carbon or nitrogen, R 1 is a radioactive halogen substituent, R 2 is a group selected from the group consisting of hydrogen, a hydroxyl group, a methoxy group, a carboxyl group, an amino group, an N-methylamino group, an N,N-dimethylamino group and a cyano group, and p is an integer of 0 to 2, provided at least one of A 1 , A 2 , A 3 and A 4 represents a carbon, and R 1 binds to a carbon represented by A 1 , A 2 , A 3 or A 4 , is effective as an image diagnosis probe targeting amyloid and a diagnostic agent for Alzheimer's disease.

  以下化合物或其盐，其化学式如下： 其中，每个A1、A2、A3和A4独立地代表碳或氮，R1是一个放射性卤素取代基，R2是从氢、羟基、甲氧基、羧基、氨基、N-甲基氨基、N,N-二甲基氨基和氰基组成的一组基团，p是0到2的整数，至少有一个A1、A2、A3和A4代表碳，且R1结合到由A1、A2、A3或A4代表的碳上，其作为靶向淀粉样蛋白的影像诊断探针和阿尔茨海默病诊断剂具有有效性。
• Novel Compound Having Affinity For Amyloid
  申请人：Tanifuji Shigeyuki

  公开号：US20100092387A1

  公开（公告）日：2010-04-15

  A compound that has affinity with amyloid, exhibits sufficiently rapid clearance from normal tissues, and is suppressed in toxicity such as mutagenicity is provided, which is represented by the following formula (1): or a salt thereof, wherein R 1 is a group selected from hydrogen, hydroxyl group, carboxyl group, sulfate group, amino group, nitro group, cyano group, an alkyl substituent with one to 4 carbon atoms or an alkoxy substituent with one to 4 carbon atoms; R 2 is a radioactive halogen substituent; and m is an integer of 0 to 2, and a low-toxic diagnostic agent for Alzheimer's disease comprising a compound represented by the above formula or a salt thereof is also provided.

  提供了一种与淀粉样物质具有亲和力、从正常组织中清除速度足够快且毒性被抑制（例如突变毒性）的化合物，该化合物由以下式子（1）表示：或其盐，其中R1是从氢、羟基、羧基、硫酸基、氨基、硝基、氰基、具有一到四个碳原子的烷基取代基或具有一到四个碳原子的烷氧基取代基中选择的基团；R2是放射性卤素取代基；m是0到2的整数。还提供了一种低毒性的阿尔茨海默病诊断剂，其包括上述式子或其盐所表示的化合物。
• Compound having affinity for amyloid
  申请人：Nihon Medi-Physics Co., Ltd.

  公开号：US08277777B2

  公开（公告）日：2012-10-02

  A compound that has affinity with amyloid, exhibits sufficiently rapid clearance from normal tissues, and is suppressed in toxicity such as mutagenicity is provided, which is represented by the following formula (1): or a salt thereof, wherein R1 is a group selected from hydrogen, hydroxyl group, carboxyl group, sulfate group, amino group, nitro group, cyano group, an alkyl substituent with one to 4 carbon atoms or an alkoxy substituent with one to 4 carbon atoms; R2 is a radioactive halogen substituent; and m is an integer of 0 to 2, and a low-toxic diagnostic agent for Alzheimer's disease comprising a compound represented by the above formula or a salt thereof is also provided.

  提供了一种与淀粉样物质具有亲和力、从正常组织中清除速度足够快且毒性被抑制，其由以下式子（1）表示：或其盐，其中R1是从氢、羟基、羧基、硫酸基、氨基、硝基、氰基、1至4个碳原子的烷基取代基或1至4个碳原子的烷氧基取代基中选择的基团；R2是放射性卤素取代基；m是0至2的整数，还提供了一种低毒性的阿尔茨海默病诊断剂，其包括上述式子或其盐所表示的化合物。