diethyl ((6-bromobenzofuran-2-yl)methyl)phosphonate | 1089682-33-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: diethyl ((6-bromobenzofuran-2-yl)methyl)phosphonate
• 英文别名: (6-bromo-1-benzofuran-2-ylmethyl)phosphonic acid diethyl ester；6-Bromo-2-(diethoxyphosphorylmethyl)-1-benzofuran
• CAS: 1089682-33-6
• 化学式: C₁₃H₁₆BrO₄P
• 分子量: 347.145
• InChiKey: LVOJLDWDQMPDSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl ((6-bromobenzofuran-2-yl)methyl)phosphonate 在 四(三苯基膦)钯 、 碘 、 sodium methylate 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 氯仿 为溶剂， 生成 (E)-5-(2-(6-iodobenzofuran-2-yl)vinyl)-N,N-dimethylpyridin-2-amine
  参考文献：
  名称：

  Structure–Activity Relationship Study of Heterocyclic Phenylethenyl and Pyridinylethenyl Derivatives as Tau-Imaging Agents That Selectively Detect Neurofibrillary Tangles in Alzheimer’s Disease Brains

  摘要：

  In order to explore novel tau-imaging agents that can selectively detect neurofibrillary tangles in Alzheimer's disease (AD) brains, we designed and synthesized a series of heterocyclic phenylethenyl and (3-pyridinyl)ethenyl derivatives with or without a dimethyl amino group. In in vitro autoradiography using AD brain sections, all radioiodinated ligands with a dimethyl amino group bound to A beta deposits in the sections. In contrast, the ligands without a dimethyl amino group showed different patterns of radioactivity accumulation in the sections depending on the kind of heterocycle contained in their molecules. Particularly, a phenylethenyl benzimidazole derivative ([I-125]64) showed marked radioactivity accumulation in the temporal lobe which corresponded with the distribution of tau deposits. [I-125]64 also showed the most favorable pharmacokinetics in normal mouse brains (3.69 and 0.06% ID/g at 2 and 60 min postinjection, respectively) among all ligands in this study. Taken together, these results suggest that [I-123]64 may be a new candidate tau-imaging agent.

  DOI：

  10.1021/acs.jmedchem.5b00440
• 作为产物：
  描述：

  4-溴-2-羟基苯甲醛 在 lithium aluminium tetrahydride 、 三溴化磷 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 29.0h， 生成 diethyl ((6-bromobenzofuran-2-yl)methyl)phosphonate
  参考文献：
  名称：

  放射性ヨウ素標識化合物、及び、これを含む放射性医薬

  摘要：

  提供同时具有τ亲和性和淀粉样蛋白亲和性的放射性碘标记化合物。本发明涉及含有N，N-二甲基苯胺基团的放射性碘标记化合物或其盐。【选择图】无

  公开号：

  JP2015089879A

文献信息

• Aminostyrylbenzofuran derivatives as potent inhibitors for Aβ fibril formation
  作者：Ji Hun Byun、HyeYun Kim、YoungSoo Kim、Inhee Mook-Jung、Dong Jin Kim、Won Koo Lee、Kyung Ho Yoo

  DOI：10.1016/j.bmcl.2008.08.111

  日期：2008.10

  The synthesis of a novel series of aminostyrylbenzofuran derivatives 1a-w and their inhibitory activities for A beta fibril formation were described. All the synthesized compounds were evaluated by thioflavin T (ThT) assay and displayed potent inhibitory activities for A beta fibril formation. Among them, compounds 1i and 1q exhibited excellent inhibitory activities (IC(50) = 0.07 and 0.08 mu M, respectively) than those of Curcumin (IC(50) = 0.80 mu M) and IMSB (IC(50) = 8.00 mu M) as reference compounds. Both compounds were selected as promising candidates for further biological evaluation. (C) 2008 Elsevier Ltd. All rights reserved.