5-fluoro-2-[1-(4-methoxybenzyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]oxazolo[5,4-b]pyridine | 1201324-17-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶唑并吡啶类
• 英文名称: 5-fluoro-2-[1-(4-methoxybenzyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]oxazolo[5,4-b]pyridine
• 英文别名: 5-fluoro-2-[1-(4-methoxy-benzyl)-1H-pyrroIo[2,3-b]pyridin-5-yl]-oxazolo[5,4-b]pyridine；5-fluoro-2-[1-(4-methoxy-benzyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-oxazolo[5,4-b]pyridine；5-fluoro-2-[1-[(4-methoxyphenyl)methyl]pyrrolo[2,3-b]pyridin-5-yl]-[1,3]oxazolo[5,4-b]pyridine
• CAS: 1201324-17-5
• 化学式: C₂₁H₁₅FN₄O₂
• 分子量: 374.374
• InChiKey: VFLIHMDGMMDEPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  66
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-fluoro-2-[1-(4-methoxybenzyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]oxazolo[5,4-b]pyridine 以 三氟乙酸 为溶剂， 反应 0.42h， 以to afford 5-fluoro-2-(1H-pyrrolo[2,3-b]pyridin-5-yl)-oxazolo[5,4-b]pyridine (2.5 mg, 9.8 μmol, 6% yield)的产率得到5-fluoro-2-(1H-pyrrolo[2,3-b]pyridin-5-yl)oxazolo[5,4-b]pyridine
  参考文献：
  名称：

  NOVEL SUBSTITUTED AZABENZOXAZOLES

  摘要：

  本发明涉及式(I)的新型淀粉样蛋白结合化合物，以及通过测量活体患者淀粉样斑块水平的变化来测量化合物效果的方法。更具体地，本发明涉及使用本发明的化合物作为正电子发射断层扫描（PET）成像中的示踪剂，以研究体内脑部淀粉样沉积物，以诊断阿尔茨海默病。因此，本发明涉及使用新型淀粉样蛋白结合化合物作为诊断工具。本发明还涉及一种测量阿尔茨海默病治疗剂临床疗效的方法。具体而言，本发明涉及新型芳基或杂芳基取代的氮杂苯并噁唑衍生物、组成物和治疗用途，以及制备这些化合物的过程，或其药学上可接受的盐、溶剂合物或体内水解酯，其中：X为O或S；A和Y独立地为N或CH。

  公开号：

  US20110085985A1
• 作为产物：
  描述：

  甲基1H-吡咯并[2,3-B]吡啶-5-甲酸酯 在 吡啶 、 1-氯-N,N,2-三甲基丙烯胺 、 sodium hydride 、 potassium carbonate 、 potassium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.17h， 生成 5-fluoro-2-[1-(4-methoxybenzyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]oxazolo[5,4-b]pyridine
  参考文献：
  名称：

  Synthesis and Evaluation of 5-Fluoro-2-aryloxazolo[5,4-b]pyridines as β-Amyloid PET Ligands and Identification of MK-3328

  摘要：

  5-Fluoro-2-aryloxazolo[5,4-b]pyridines were synthesized and investigated as potential F-18 containing beta-amyloid PET ligands. In competition binding assays using human AD brain homogenates, compounds 14b, 16b, and 17b were identified as having favorable potency versus human beta-amyloid plaque and were radiolabeled for further evaluation in in vitro binding and in vivo PET imaging experiments. These studies led to the identification of 17b (MK-3328) as a candidate PET ligand for the clinical assessment of beta-amyloid plaque load.

  DOI：

  10.1021/ml200018n

文献信息

• NOVEL SUBSTITUTED AZABENZOXAZOLES
  申请人：Barrow James C.

  公开号：US20110085985A1

  公开（公告）日：2011-04-14

  The present invention relates to novel amyloid binding compounds of formula (I) and methods for measuring effects of the compounds, by measuring changes of amyloid plaque level in living patients. More specifically, the present invention relates to a method of using the compounds of this invention as tracers in positron emission tomography (PET/) imaging to study amyloid deposits in brain in vivo to allow diagnosis of Alzheimer's disease. Thus, the present invention relates to use of the novel amyloid binding compounds as a diagnostic. The invention further relates to a method of measuring clinical efficacy of Alzheimer's disease therapeutic agents. Specifically, the present invention relates to novel aryl or heteroaryl substituted azabenzoxazole derivatives, compositions, and therapeutic uses and processes for making such compounds, or a pharmaceutically acceptable salt, solvate or in vivo hydrolysable ester thereof, wherein: X is O or S; A and Y independently are N, or CH;

  本发明涉及式(I)的新型淀粉样蛋白结合化合物，以及通过测量活体患者淀粉样斑块水平的变化来测量化合物效果的方法。更具体地，本发明涉及使用本发明的化合物作为正电子发射断层扫描（PET）成像中的示踪剂，以研究体内脑部淀粉样沉积物，以诊断阿尔茨海默病。因此，本发明涉及使用新型淀粉样蛋白结合化合物作为诊断工具。本发明还涉及一种测量阿尔茨海默病治疗剂临床疗效的方法。具体而言，本发明涉及新型芳基或杂芳基取代的氮杂苯并噁唑衍生物、组成物和治疗用途，以及制备这些化合物的过程，或其药学上可接受的盐、溶剂合物或体内水解酯，其中：X为O或S；A和Y独立地为N或CH。
• Substituted azabenzoxazoles
  申请人：Barrow James C.

  公开号：US08530483B2

  公开（公告）日：2013-09-10

  The present invention relates to novel amyloid binding compounds of formula (I) and methods for measuring effects of the compounds, by measuring changes of amyloid plaque level in living patients. More specifically, the present invention relates to a method of using the compounds of this invention as tracers in positron emission tomography (PET/) imaging to study amyloid deposits in brain in vivo to allow diagnosis of Alzheimer's disease. Thus, the present invention relates to use of the novel amyloid binding compounds as a diagnostic. The invention further relates to a method of measuring clinical efficacy of Alzheimer's disease therapeutic agents. Specifically, the present invention relates to novel aryl or heteroaryl substituted azabenzoxazole derivatives, compositions, and therapeutic uses and processes for making such compounds, or a pharmaceutically acceptable salt, solvate or in vivo hydrolysable ester thereof, wherein: X is O or S; A and Y independently are N, or CH.

  本发明涉及公式（I）的新型淀粉样结合化合物以及通过测量活体患者淀粉样斑块水平的变化来测量化合物效果的方法。更具体地说，本发明涉及使用本发明中的化合物作为正电子发射断层扫描（PET）成像中的示踪剂来研究体内脑部淀粉样沉积物，以允许诊断阿尔茨海默病的方法。因此，本发明涉及将新型淀粉样结合化合物用作诊断工具。本发明还涉及测量阿尔茨海默病治疗剂临床疗效的方法。具体而言，本发明涉及新型芳基或杂环芳基取代的氮杂苯并噁唑衍生物、组成物和治疗用途以及制备这种化合物的过程，或其药学上可接受的盐、溶剂合物或体内可水解的酯。其中：X为O或S；A和Y分别为N或CH。
• [EN] NOVEL SUBSTITUTED AZABENZOXAZOLES<br/>[FR] NOUVEAUX AZABENZOXAZOLES SUBSTITUÉS
  申请人：MERCK SHARP & DOHME

  公开号：WO2009155017A3

  公开（公告）日：2010-02-18
• US8530483B2
  申请人：——

  公开号：US8530483B2

  公开（公告）日：2013-09-10
• Synthesis and Evaluation of 5-Fluoro-2-aryloxazolo[5,4-<i>b</i>]pyridines as β-Amyloid PET Ligands and Identification of MK-3328
  作者：Scott T. Harrison、James Mulhearn、Scott E. Wolkenberg、Patricia J. Miller、Stacey S. O’Malley、Zhizhen Zeng、David L. Williams、Eric D. Hostetler、Sandra Sanabria-Bohórquez、Linda Gammage、Hong Fan、Cyrille Sur、J. Christopher Culberson、Richard J. Hargreaves、Jacquelynn J. Cook、George D. Hartman、James C. Barrow

  DOI：10.1021/ml200018n

  日期：2011.7.14

  5-Fluoro-2-aryloxazolo[5,4-b]pyridines were synthesized and investigated as potential F-18 containing beta-amyloid PET ligands. In competition binding assays using human AD brain homogenates, compounds 14b, 16b, and 17b were identified as having favorable potency versus human beta-amyloid plaque and were radiolabeled for further evaluation in in vitro binding and in vivo PET imaging experiments. These studies led to the identification of 17b (MK-3328) as a candidate PET ligand for the clinical assessment of beta-amyloid plaque load.