2-(6-(dimethylamino)pyridin-3-yl)benzofuran-5-ol | 1255926-33-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 2-(6-(dimethylamino)pyridin-3-yl)benzofuran-5-ol
• 英文别名: 2-[6-(Dimethylamino)pyridin-3-yl]-1-benzofuran-5-ol
• CAS: 1255926-33-0
• 化学式: C₁₅H₁₄N₂O₂
• 分子量: 254.288
• InChiKey: MYZIKPFOTOEADM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  49.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(6-(dimethylamino)pyridin-3-yl)benzofuran-5-ol 在 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 30.0h， 生成 tert-butyl 2-((3-(2-(6-(dimethylamino)pyridin-3-yl)benzofuran-6-yloxy)propyl)(2-(tritylthio)ethyl)amino)ethyl(2-(tritylthio)ethyl)carbamate
  参考文献：
  名称：

  JP5825608

  摘要：

  公开号：
• 作为产物：
  描述：

  5-(5-methoxy-1-benzofuran-2-yl)-N,N-dimethylpyridin-2-amine 在 三溴化硼 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以98.9%的产率得到2-(6-(dimethylamino)pyridin-3-yl)benzofuran-5-ol
  参考文献：
  名称：

  net 99m标记的吡啶基苯并呋喃衍生物作为阿尔茨海默氏症大脑中β淀粉样蛋白斑块的单光子发射计算机断层成像成像探针

  摘要：

  测试了三种新颖的99m Tc标记的吡啶基苯并呋喃衍生物，作为使用单光子发射计算机断层扫描（SPECT）对β-淀粉样蛋白斑进行成像的潜在探针。的99米Tc和对应铼复合物用双（氨基乙硫醇）（BAT）作为螯合配体合成。所有Re复合物均显示出对Aβ（1-42）聚集体的亲和力（K i = 13.6-149.6 nM）。在正常小鼠中进行的生物分布实验表明，99m Tc标记的衍生物在大脑中显示出足够的摄取（注射后2分钟为1.41–1.80％ID / g）。值得注意的是，[ 99mTc] BAT-Bp-2表现出良好的初始摄取（2分钟时为1.80％ID / g）和合理的脑液冲洗（60分钟时为0.79％ID / g）。用[ 99m Tc] BAT-Bp-2进行的放射自显影显示，在Tg2576转基因小鼠的脑组织切片中，β-淀粉样斑块有大量标记，而在年龄匹配的对照中则没有。[ 99m Tc] BAT-Bp-2可能

  DOI：

  10.1021/jm201513c

文献信息

• (R)- and (S)-18F-labeled 2-arylbenzofurans with improved pharmacokinetics as β-amyloid imaging probes
  作者：Jia Song、Xiaoyang Zhang、Yunling Zhao、Hui Yang、Jinming Zhang、Xiaojun Zhang、Jiapei Dai、Mengchao Cui

  DOI：10.1016/j.ejmech.2017.03.073

  日期：2017.7

  mouse and AD human brain tissue after labeled by 18F. The purified enantiomers displayed apparent discrepancy in biodistribution experiments in normal mice, for (S)-enantiomers provided rather faster clearance than (R)-enantiomers. All in all, (S)-[18F]17 (Ki = 14.6 nM) with excellent pharmacokinetics (brain2 min = 8.60% ID/g, brain2 min/brain60 min = 14.1) deserves further evaluation.

  合成了一类新型的2-芳基苯并呋喃衍生物的光学异构体，并将其评估为潜在的β-淀粉样蛋白斑成像剂。亲脂性和信噪比都大大改善了手性羟基添加到1-氟-3-（氧代烷基）丙烷-2-醇侧链。这些衍生物显示出对Aβ1-42聚集体的中等至高结合亲和力。选择了四个具有强结合亲和力（Ki <30 nM）的示踪剂用于进一步研究。在体外放射自显影研究中，四种探针在18F标记后显示出与Tg小鼠和AD人脑组织中Aβ斑块的有效结合。纯化的对映异构体在正常小鼠的生物分布实验中显示出明显的差异，因为（S）-对映异构体提供的清除速度比（R）-对映异构体快。总计，（S）-[18F] 17（Ki = 14。
• Novel radiogallium-labeled pyridyl benzofuran derivative for detection of amylin aggregates in pancreas
  作者：Hiroyuki Watanabe、Kiyoshiro Kawano、Shimpei Iikuni、Yoichi Shimizu、Masahiro Ono

  DOI：10.1016/j.nucmedbio.2020.10.003

  日期：2020.11

  Introduction: The deposition of islet amyloid composed of amylin aggregates is related to β-cell mass dysfunction in type 2 diabetes mellitus (T2DM), and it may be involved in the development and progression of T2DM. In this study, we newly designed, synthesized, and evaluated a radiogallium-labeled pyridyl benzofuran derivative ([^67/68Ga]GPBF) as an amylin imaging probe. Methods: An in vitro competitive inhibition assay was performed to determine the binding affinity for amylin aggregates. An in vitro autoradiographic study was carried out using pancreatic sections from a T2DM patient. A biodistribution of [⁶⁷Ga]GPBF in normal mice was evaluated. Finally, we carried out ex vivo autoradiography using mouse transplanted with amylin aggregates. Results: GPBF exhibited binding affinity for amylin aggregates in vitro. In addition, [⁶⁷Ga]GPBF clearly labeled islet amyloids in in vitro autoradiography of a T2DM pancreatic section. In a biodistribution study using normal mice, [⁶⁷Ga]GPBF showed initial uptake into the pancreas, but non-specific accumulation in the liver, spleen, and pancreas was also observed. Furthermore, an ex vivo autoradiogram demonstrated that [⁶⁷Ga]GPBF bound to amylin aggregates in the pancreas of the amylin aggregate-transplanted mice. Conclusions: These results provide useful insights into the development of radiogallium labeled probes that target amylin aggregates in the T2DM pancreas.
• A novel 18F-labeled pyridyl benzofuran derivative for imaging of β-amyloid plaques in Alzheimer’s brains
  作者：Yan Cheng、Masahiro Ono、Hiroyuki Kimura、Shinya Kagawa、Ryuichi Nishii、Hideo Saji

  DOI：10.1016/j.bmcl.2010.08.016

  日期：2010.10

  A potential probe for PET targeting beta-amyloid plaques in Alzheimer's disease (AD) brain, FPYBF-1 (5-(5-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)benzofuran-2-yl)-N,N-dimethylpyridin-2-amine), was synthesized and evaluated. In experiments in vitro, FPYBF-1 displayed high affinity for A beta(1-42) aggregates (K-i = 0.9 nM), and substantial labeling of beta-amyloid plaques in sections of postmortem AD brains but not control brains. In experiments in vivo, [F-18]FPYBF-1 displayed good initial uptake (5.16%ID/g at 2 min postinjection) and rapid washout from the brain (2.44%ID/g at 60 min postinjection) in normal mice, and excellent binding to beta-amyloid plaques in a murine model of AD. Furthermore, the specific labeling of plaques labeling was observed in autoradiographs of autopsied AD brain sections. [F-18] FPYBF-1 may be a useful probe for imaging beta-amyloid plaques in living brain tissue. (C) 2010 Elsevier Ltd. All rights reserved.
• [EN] PYRIDYL BENZOFURAN DERIVATIVE<br/>[FR] DÉRIVÉ DE PYRIDYLBENZOFURANNE
  申请人：UNIV KYOTO

  公开号：WO2012017891A1

  公开（公告）日：2012-02-09

  　本発明は、ピリジルベンゾフラン誘導体および前記誘導体を含むアミロイド関連疾患診断用組成物に関する。