2-(1,3-benzodioxol-5-yl)-1-(4-hydroxyphenyl)-4-oxobutyric acid methyl ester | 1196878-79-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2-(1,3-benzodioxol-5-yl)-1-(4-hydroxyphenyl)-4-oxobutyric acid methyl ester
• CAS: 1196878-79-1
• 化学式: C₁₈H₁₆O₆
• 分子量: 328.321
• InChiKey: UOOCZNJJXJUVEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.65
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  82.06
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-(1,3-benzodioxol-5-yl)-1-(4-hydroxyphenyl)-4-oxobutyric acid methyl ester 、 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 20.0h， 以64%的产率得到2-(1,3-benzodioxol-5-yl)-1-[4-(2-bromoethoxy)phenyl]-4-oxobutyric acid methyl ester
  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
• 作为产物：
  描述：

  2-(benzo[1,3]dioxol-5-yl)-1-(4-benzyloxyphenyl)-4-oxobutyric acid methyl ester 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 48.0h， 以83%的产率得到2-(1,3-benzodioxol-5-yl)-1-(4-hydroxyphenyl)-4-oxobutyric acid methyl ester
  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