3-(2-bromoethoxy)-4,5-dimethoxybenzaldehyde | 1196878-62-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(2-bromoethoxy)-4,5-dimethoxybenzaldehyde
• 英文别名: 3-(2-Bromoethoxy)-4,5-dimethoxybenzaldehyde
• CAS: 1196878-62-2
• 化学式: C₁₁H₁₃BrO₄
• 分子量: 289.126
• InChiKey: NQMLPIXUMWITAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-bromoethoxy)-4,5-dimethoxybenzaldehyde 在 sodium 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 43.0h， 生成 2-(5-{[4-(benzo[1,3]dioxol-5-yl)-2-hydroxy-2-(4-methoxyphenyl)-5-oxo-2,5-dihydrofuran-3-yl]methyl}-2,3-dimethoxyphenoxy)ethyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  正电子发射体层摄影术中内皮素A受体（放射性）配体的开发和评估

  摘要：

  内皮素（ET）受体的表达和功能在心血管疾病，肿瘤进展和肿瘤转移中异常。先前报道的基于非肽ET A受体拮抗剂PD 156707的用于正电子发射断层扫描（PET）的有前途的放射性配体显示出与心肌中靶标受体的特异性结合，但在胆汁和肠中高积累，这可能是由于其高亲脂性。在这项研究中，我们描述了一系列具有亲水结构单元的氟化衍生物的合成。所有化合物被评估为高亲和力ET甲受体配体（16，17，23 - 26，ķ我= 1.4−7.9 nM），并且具有比ET B受体更高的亚型选择性。[ 18 F] 3-苯并[1,3]二氧杂环戊烯-5-基-4- {3- [1-（2- {2- [2-（2-氟乙氧基）乙氧基]乙氧基}乙基）-1- ħ -合成了[1,2,3]三唑-4-基甲氧基] -4,5-二甲氧基苄基} -5-羟基-5-（4-甲氧基苯基）-5 H-呋喃-2-酮（[ 18 F] 17）作为该系列的放射性配体之一，在人血

  DOI：

  10.1021/jm101110w
• 作为产物：
  描述：

  3,4-二甲氧基-5-羟基苯甲醛 、 1,2-二溴乙烷 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以69%的产率得到3-(2-bromoethoxy)-4,5-dimethoxybenzaldehyde
  参考文献：
  名称：

  PET-compatible endothelin receptor radioligands: Synthesis and first in vitro and in vivo studies

  摘要：

  The expression and function of endothelin (ET) receptors is abnormal in cardiovascular diseases, tumor progression, and tumor metastasis. In this study, we prepared two [F-18]-fluorinated derivatives of the non-peptide ETA receptor antagonist PD 156707 and evaluated their ET receptor binding potencies. Ex vivo as well as in vivo biodistribution studies in mice were performed, as well as the metabolism of the radiotracer, which was examined by metabolite analysis in mice and rats. All tested derivatives of PD 156707 exhibited potent in vitro pharmacological characteristics with K-i values comparable to that of the lead compound. The biodistribution studies showed a high accumulation of the tracer in bile and intestine. In vivo we were able to show that the visualization of the heart as a major target organ with high ETAR expression is possible. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.08.058

文献信息

• Development and Evaluation of Endothelin-A Receptor (Radio)Ligands for Positron Emission Tomography
  作者：Kristin Michel、Katrin Büther、Marilyn P. Law、Stefan Wagner、Otmar Schober、Sven Hermann、Michael Schäfers、Burkhard Riemann、Carsten Höltke、Klaus Kopka

  DOI：10.1021/jm101110w

  日期：2011.2.24

  tumor metastasis. A previously reported promising radioligand for positron emission tomography (PET) based on the non-peptide ETA receptor antagonist PD 156707 showed specific binding to target receptors in the myocardium but high accumulation in bile and intestine, probably because of its high lipophilicity. In this study we describe the synthesis of a series of fluorinated derivatives with hydrophilic

  内皮素（ET）受体的表达和功能在心血管疾病，肿瘤进展和肿瘤转移中异常。先前报道的基于非肽ET A受体拮抗剂PD 156707的用于正电子发射断层扫描（PET）的有前途的放射性配体显示出与心肌中靶标受体的特异性结合，但在胆汁和肠中高积累，这可能是由于其高亲脂性。在这项研究中，我们描述了一系列具有亲水结构单元的氟化衍生物的合成。所有化合物被评估为高亲和力ET甲受体配体（16，17，23 - 26，ķ我= 1.4−7.9 nM），并且具有比ET B受体更高的亚型选择性。[ 18 F] 3-苯并[1,3]二氧杂环戊烯-5-基-4- 3- [1-（2- 2- [2-（2-氟乙氧基）乙氧基]乙氧基}乙基）-1- ħ -合成了[1,2,3]三唑-4-基甲氧基] -4,5-二甲氧基苄基} -5-羟基-5-（4-甲氧基苯基）-5 H-呋喃-2-酮（[ 18 F] 17）作为该系列的放射性配体之一，在人血
• PET-compatible endothelin receptor radioligands: Synthesis and first in vitro and in vivo studies
  作者：Carsten Höltke、Marilyn P. Law、Stefan Wagner、Klaus Kopka、Andreas Faust、Hans-Jörg Breyholz、Otmar Schober、Christoph Bremer、Burkhard Riemann、Michael Schäfers

  DOI：10.1016/j.bmc.2009.08.058

  日期：2009.10

  The expression and function of endothelin (ET) receptors is abnormal in cardiovascular diseases, tumor progression, and tumor metastasis. In this study, we prepared two [F-18]-fluorinated derivatives of the non-peptide ETA receptor antagonist PD 156707 and evaluated their ET receptor binding potencies. Ex vivo as well as in vivo biodistribution studies in mice were performed, as well as the metabolism of the radiotracer, which was examined by metabolite analysis in mice and rats. All tested derivatives of PD 156707 exhibited potent in vitro pharmacological characteristics with K-i values comparable to that of the lead compound. The biodistribution studies showed a high accumulation of the tracer in bile and intestine. In vivo we were able to show that the visualization of the heart as a major target organ with high ETAR expression is possible. (C) 2009 Elsevier Ltd. All rights reserved.