8-fluoropyrazino[2,3-c]quinolin-5(6H)-one | 1439364-69-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 8-fluoropyrazino[2,3-c]quinolin-5(6H)-one
• 英文别名: 8-fluoro-6H-pyrazino[2,3-c]quinolin-5-one
• CAS: 1439364-69-8
• 化学式: C₁₁H₆FN₃O
• 分子量: 215.187
• InChiKey: GGOBRBINDAXSKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-fluoropyrazino[2,3-c]quinolin-5(6H)-one 在 草酰氯 、 lithium hexamethyldisilazane 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 8-fluoro-5-(1-propylpiperidin-4-yl)methyloxypyrazino[2,3-c]quinoline
  参考文献：
  名称：

  Design of a serotonin 4 receptor radiotracer with decreased lipophilicity for single photon emission computed tomography

  摘要：

  With the aim to develop a suitable radiotracer for the brain imaging of the serotonin 4 receptor subtype (5-HT4R) using single photon emission computed tomography (SPECT), we synthesized and evaluated a library of di- and triazaphenanthridines with lipophilicity values which were in the range expected to favour brain penetration, and which demonstrated specific binding to the target of interest. Adding additional nitrogen atoms to previously described phenanthridine ligands exhibiting a high unspecific binding, we were able to design a radioiodinated compound [I-125]14. This compound exhibited a binding affinity value of 0.094 nM toward human 5-HT4R and a high selectivity over other serotonin receptor subtypes (5-HTR). In vivo SPECS imaging studies and competition experiments demonstrated that the decreased lipophilicity (in comparison with our previously reported compounds 4 and 5) allowed a more specific labelling of the 5-HT4R brain-containing regions. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.03.017
• 作为产物：
  描述：

  3-(2',4'-difluorophenyl)pyrazine-2-carbonitrile 在 potassium hydroxide 作用下， 以 叔丁醇 为溶剂， 反应 1.5h， 以97%的产率得到8-fluoropyrazino[2,3-c]quinolin-5(6H)-one
  参考文献：
  名称：

  取代的重氮[ c ]喹啉-5（6 H）-one，重氮[ c ]异喹啉-6（5 H）-one，重氮[ c ]萘啶-6（5 H）-one和重氮[ c ]萘啶的合成。-5（6 H）-个

  摘要：

  使用以下方法获得取代的重氮[ c ]喹啉-5（6 H）-one和-异喹啉-6（5 H）-one，重氮[ c ]萘啶-6（5 H）-和-5（6 H）-one。两种合成途径：一锅交叉偶联/环化和两步交叉偶联/ KOH介导的阴离子闭环。两种策略产生的收率处于相同的数量级，其选择取决于起始物料的可用性。

  DOI：

  10.1016/j.tet.2013.04.104

文献信息

• Synthesis of substituted diazino[c]quinolin-5(6H)-ones, diazino[c]isoquinolin-6(5H)-ones, diazino[c]naphthyridin-6(5H)-ones and diazino[c]naphthyridin-5(6H)-ones
  作者：Nathalie Fresneau、Thomas Cailly、Frédéric Fabis、Jean-Philippe Bouillon

  DOI：10.1016/j.tet.2013.04.104

  日期：2013.7

  Substituted diazino[c]quinolin-5(6H)-ones and -isoquinolin-6(5H)-ones, diazino[c]naphthyridin-6(5H)- and -5(6H)-ones were obtained using two synthetic routes: one-pot cross-coupling/cyclisation and two-step cross-coupling/KOH-mediated anionic ring closure. The two strategies gave yields in the same order of magnitude and their choice depends on the availability of the starting material.

  使用以下方法获得取代的重氮[ c ]喹啉-5（6 H）-one和-异喹啉-6（5 H）-one，重氮[ c ]萘啶-6（5 H）-和-5（6 H）-one。两种合成途径：一锅交叉偶联/环化和两步交叉偶联/ KOH介导的阴离子闭环。两种策略产生的收率处于相同的数量级，其选择取决于起始物料的可用性。
• Design of a serotonin 4 receptor radiotracer with decreased lipophilicity for single photon emission computed tomography
  作者：Nathalie Fresneau、Noé Dumas、Benjamin B. Tournier、Christine Fossey、Céline Ballandonne、Aurélien Lesnard、Philippe Millet、Yves Charnay、Thomas Cailly、Jean-Philippe Bouillon、Frédéric Fabis

  DOI：10.1016/j.ejmech.2015.03.017

  日期：2015.4

  With the aim to develop a suitable radiotracer for the brain imaging of the serotonin 4 receptor subtype (5-HT4R) using single photon emission computed tomography (SPECT), we synthesized and evaluated a library of di- and triazaphenanthridines with lipophilicity values which were in the range expected to favour brain penetration, and which demonstrated specific binding to the target of interest. Adding additional nitrogen atoms to previously described phenanthridine ligands exhibiting a high unspecific binding, we were able to design a radioiodinated compound [I-125]14. This compound exhibited a binding affinity value of 0.094 nM toward human 5-HT4R and a high selectivity over other serotonin receptor subtypes (5-HTR). In vivo SPECS imaging studies and competition experiments demonstrated that the decreased lipophilicity (in comparison with our previously reported compounds 4 and 5) allowed a more specific labelling of the 5-HT4R brain-containing regions. (C) 2015 Elsevier Masson SAS. All rights reserved.