2-bromo-3-(2-fluoroethoxy)pyridine | 1352725-59-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-bromo-3-(2-fluoroethoxy)pyridine
• CAS: 1352725-59-7
• 化学式: C₇H₇BrFNO
• 分子量: 220.041
• InChiKey: JIGVGJWRCLOING-UHFFFAOYSA-N

物化性质

• 沸点：
  271.9±30.0 °C(Predicted)
• 密度：
  1.519±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险性描述：
  H315,H319

反应信息

• 作为反应物：
  描述：

  2-bromo-3-(2-fluoroethoxy)pyridine 在 正丁基锂 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 45.0h， 生成 (3-(2-fluoroethoxy)pyridin-2-yl)(1-(3-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)piperidin-4-yl)methanone oxalate
  参考文献：
  名称：

  Heteroaromatic and Aniline Derivatives of Piperidines As Potent Ligands for Vesicular Acetylcholine Transporter

  摘要：

  To identify suitable lipophilic compounds having high potency and selectivity for vesicular acetylcholine transporter (VAChT), a heteroaromatic ring or a phenyl group was introduced into the carbonyl-containing scaffold for VAChT ligands. Twenty new compounds with ALogD values between 0.53 and 3.2 were synthesized, and their in vitro binding affinities were assayed. Six of them (19a, 19e, 19g, 19k, and 24a-b) displayed high affinity for VAChT (K-i = 0.93-18 nM for racemates) and moderate to high selectivity for VAChT over sigma(1) and sigma(2) receptors (K-i = 44-4400-fold). These compounds have a methyl or a fluoro substitution that provides the position for incorporating PET radioisotopes C-11 or F-18. Compound (-)-[C-11]24b (K-i = 0.78 nM for VAChT, 1200-fold over sigma receptors) was successfully synthesized and evaluated in vivo in rats and nonhuman primates. The data revealed that (-)-[C-11]24b has highest binding in striatum and has favorable pharmacokinetics in the brain.

  DOI：

  10.1021/jm400664x
• 作为产物：
  描述：

  2-溴-3-羟基吡啶 、 1-溴-2-氟乙烷 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 以68%的产率得到2-bromo-3-(2-fluoroethoxy)pyridine
  参考文献：
  名称：

  Compounds comprising 4-benzoylpiperidine as a Sigma-1-selective ligand

  摘要：

  双哌啶基化合物及其盐被披露。这些化合物包括对σ1受体具有高亲和力的配体。一些化合物相对于σ2受体也具有高选择性。化合物可以包含放射性同位素，包括18F或11C。放射标记的化合物可用作探针，用于通过正电子发射断层扫描（PET扫描）在受试者（如人类）中成像σ1受体的分布。

  公开号：

  US20110311447A1

文献信息

• Compounds comprising 4-benzoylpiperidine as a Sigma-1-selective ligand
  申请人：Tu Zhude

  公开号：US20110311447A1

  公开（公告）日：2011-12-22

  Bipiperidinyl compounds and salts thereof are disclosed. The compounds include high affinity ligands for σ 1 receptors. Some compounds are also highly selective for σ 1 receptor compared to σ 2 receptor. Compounds can comprise radioisotopes, including 18 F or 11 C. Radiolabeled compounds can be used as probes for imaging distribution of σ 1 receptor in a subject such as a human using positron emission tomography (PET) scanning.

  双哌啶基化合物及其盐被披露。这些化合物包括对σ1受体具有高亲和力的配体。一些化合物相对于σ2受体也具有高选择性。化合物可以包含放射性同位素，包括18F或11C。放射标记的化合物可用作探针，用于通过正电子发射断层扫描（PET扫描）在受试者（如人类）中成像σ1受体的分布。
• Compounds comprising 4-benzoylpiperidine as a sigma-1-selective ligand
  申请人：Tu Zhude

  公开号：US08658131B2

  公开（公告）日：2014-02-25

  Bipiperidinyl compounds and salts thereof are disclosed. The compounds include high affinity ligands for σ1 receptors. Some compounds are also highly selective for σ1 receptor compared to σ2 receptor. Compounds can comprise radioisotopes, including 18F or 11C. Radiolabeled compounds can be used as probes for imaging distribution of σ1 receptor in a subject such as a human using positron emission tomography (PET) scanning.

  本文披露了Bipiperidinyl化合物及其盐。这些化合物包括σ1受体的高亲和力配体。一些化合物与σ2受体相比高度选择性地作用于σ1受体。化合物可以包含放射性同位素，包括18F或11C。放射性标记的化合物可用作探针，通过正电子发射断层扫描（PET扫描）成像研究主体（如人体）中σ1受体的分布。
• US8658131B2
  申请人：——

  公开号：US8658131B2

  公开（公告）日：2014-02-25
• Heteroaromatic and Aniline Derivatives of Piperidines As Potent Ligands for Vesicular Acetylcholine Transporter
  作者：Junfeng Li、Xiang Zhang、Zhanbin Zhang、Prashanth K. Padakanti、Hongjun Jin、Jinquan Cui、Aixiao Li、Dexing Zeng、Nigam P. Rath、Hubert Flores、Joel S. Perlmutter、Stanley M. Parsons、Zhude Tu

  DOI：10.1021/jm400664x

  日期：2013.8.8

  To identify suitable lipophilic compounds having high potency and selectivity for vesicular acetylcholine transporter (VAChT), a heteroaromatic ring or a phenyl group was introduced into the carbonyl-containing scaffold for VAChT ligands. Twenty new compounds with ALogD values between 0.53 and 3.2 were synthesized, and their in vitro binding affinities were assayed. Six of them (19a, 19e, 19g, 19k, and 24a-b) displayed high affinity for VAChT (K-i = 0.93-18 nM for racemates) and moderate to high selectivity for VAChT over sigma(1) and sigma(2) receptors (K-i = 44-4400-fold). These compounds have a methyl or a fluoro substitution that provides the position for incorporating PET radioisotopes C-11 or F-18. Compound (-)-[C-11]24b (K-i = 0.78 nM for VAChT, 1200-fold over sigma receptors) was successfully synthesized and evaluated in vivo in rats and nonhuman primates. The data revealed that (-)-[C-11]24b has highest binding in striatum and has favorable pharmacokinetics in the brain.