1-(5-bromo-2-hydroxyphenyl)-3-(4-nitrophenyl)pent-4-ene-1,3-dione | 919299-19-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(5-bromo-2-hydroxyphenyl)-3-(4-nitrophenyl)pent-4-ene-1,3-dione
• 英文别名: 1-(5-bromo-2-hydroxyphenyl)-5-(4-nitrophenyl)pent-4-ene-1,3-dione；1-(5-bromo-2-hydroxyphenyl)-5-(4-nitrophenyl)pento-4-en-1,3-dione；(E)-1-(5-bromo-2-hydroxyphenyl)-5-(4-nitrophenyl)pent-4-ene-1,3-dione
• CAS: 919299-19-7
• 化学式: C₁₇H₁₂BrNO₅
• 分子量: 390.19
• InChiKey: WUIOTVJTUHGGPP-XVNBXDOJSA-N

物化性质

• 沸点：
  547.1±50.0 °C(Predicted)
• 密度：
  1.583±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(5-bromo-2-hydroxyphenyl)-3-(4-nitrophenyl)pent-4-ene-1,3-dione 在 四(三苯基膦)钯 硫酸 、 溶剂黄146 、 三乙胺 、 tin(ll) chloride 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 9.17h， 生成 6-iodo-2-(4'-aminostyryl)chromone
  参考文献：
  名称：

  Synthesis and characterization of styrylchromone derivatives as β-amyloid imaging agents

  摘要：

  Several promising agents have been synthesized and evaluated for in vivo imaging probes of P-amyloid plaques in Alzheimer's disease (AD) brain. Recently, we have developed flavone derivatives, which possess the basic structure of the 2-phenylchromone, as useful candidates for amyloid imaging agents. In an attempt to further develop novel tracers, we synthesized and evaluated a series of 2-styrylchromone derivatives, which replace the 2-phenyl substituent of flavone backbone with the 2-styryl. A series of radioiodinated styrylchromone derivatives were designed and synthesized. The binding affinities for amyloid plaques were assessed by in vitro binding assay using pre-formed synthetic A beta(1-40) aggregates. The new series of styrylchromone derivatives showed high binding affinity to A beta aggregates at the K-d values of 32.0, 17.5 and 8.7 nM for [I-125]6, [I-125]9, and [I-125]12, respectively. In biodistribution studies using normal mice, [I-125]6 and [I-125]9 examined in normal mice displayed high brain uptakes with 4.9 and 2.8%ID/g at 2 min post injection. The radioactivity washed out from the brain rapidly (1.6 and 1.0%ID/g at 60 min post injection for [I-125]6 and [I-125]9, respectively). But [I-125]12 did not show marked brain uptake, and the washout rate from the brain was relatively slow throughout the time course (1.1 and 1.4%ID/g at 2 and 30 min post injection, respectively). Although additional modifications are necessary to improve the brain uptake and rapid clearance of non-specifically bound radiotracer, the styrylchromone backbone may be useful as a backbone structure to develop novel beta-amyloid imaging agents. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.044
• 作为产物：
  描述：

  2-羟基-5-溴苯乙酮 在 吡啶 、 溶剂黄146 、 potassium hydroxide 作用下， 反应 2.5h， 生成 1-(5-bromo-2-hydroxyphenyl)-3-(4-nitrophenyl)pent-4-ene-1,3-dione
  参考文献：
  名称：

  アミロイドβ疾患のホウ素中性子捕捉療法用化合物

  摘要：

  针对β淀粉样蛋白具有高结合特异性、高血脑屏障透过性和在脑内老年斑中具有积累性，同时具有不易残留在脑内老年斑以外部位的硼载体化合物。通过在类黄酮衍生物、香豆素衍生物、香豆素衍生物、噁罗衍生物、查尔酮衍生物、苯并噻唑衍生物和白藜芦醇衍生物中含有硼-10原子来提供用于β淀粉样或病理性淀粉样蛋白相关疾病的硼中子俘获疗法的化合物及其用途。【选择图】无

  公开号：

  JP2020066619A

文献信息

• Composition For Diagnosing Amyloid-Related Diseases
  申请人：Mori Hiroshi

  公开号：US20080131367A1

  公开（公告）日：2008-06-05

  A composition for diagnosing amyloid-related diseases, which comprises a flavone derivative, a chalcone derivative, a styrylchromone derivative, or a coumarin derivative, is provided. These compounds have high binding specificity to an amyloid β protein, high permeability to a blood-brain barrier, and ability to rapidly disappear from sites other than cerebral senile plaque. Accordingly, the composition of the present invention using these compounds enables the diagnosis of amyloid-related diseases with high precision.

  本发明提供了一种用于诊断淀粉样相关疾病的组合物，其中包括一种黄酮衍生物、一种查尔酮衍生物、一种苯乙烯基色酮衍生物或一种香豆素衍生物。这些化合物具有高结合特异性，能够与淀粉样β蛋白结合，具有高渗透性到血脑屏障，并能够迅速从除脑部老年斑以外的其他部位消失。因此，使用这些化合物的本发明组合物能够高精度地诊断淀粉样相关疾病。
• EP1815872
  申请人：——

  公开号：——

  公开（公告）日：——
• US8192717B2
  申请人：——

  公开号：US8192717B2

  公开（公告）日：2012-06-05