1-(5-溴-2-羟基苯基)-3-(4-甲氧基苯基)丙烷-1,3-二酮 | 88952-44-7

• 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
• 中文名称: 1-(5-溴-2-羟基苯基)-3-(4-甲氧基苯基)丙烷-1,3-二酮
• 英文名称: 1-(5-bromo-2-hydroxyphenyl)-3-(4-methoxyphenyl)propane-1,3-dione
• 英文别名: 1,3-Propanedione, 1-(5-bromo-2-hydroxyphenyl)-3-(4-methoxyphenyl)-
• CAS: 88952-44-7
• 化学式: C₁₆H₁₃BrO₄
• 分子量: 349.181
• InChiKey: BEOPPHIBRDRGPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(5-溴-2-羟基苯基)-3-(4-甲氧基苯基)丙烷-1,3-二酮 在 硫酸 、 三溴化硼 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 6-溴-4-羟基黄酮
  参考文献：
  名称：

  Radioiodinated Flavones for in Vivo Imaging of β-Amyloid Plaques in the Brain

  摘要：

  In vivo imaging of beta-amyloid (A beta) peptide aggregates in the brain may lead to early detection of Alzheimer's disease (AD) and monitoring of the progression and effectiveness of AD treatment. The purpose of this study was to develop novel amyloid imaging agents based on flavone as a core structure. Radioiodinated flavone derivatives were designed and synthesized. The binding affinities of flavone derivatives for A beta aggregates varied from 13 to 77 nM. When in vitro plaque labeling was carried out using post-mortem AD brain sections, all flavones intensely stained not only amyloid plaques but also cerebrovascular amyloids. In biodistribution studies using normal mice, they displayed high brain uptakes ranging from 3.2 to 4.1% ID/g at 2 min postinjection. The radioactivity washed out from the brain rapidly (0.5-1.9% ID/g at 30 min), which is highly desirable for amyloid imaging agents. The results in the study suggest that these classes of radioiodinated flavones may be useful candidates as potential imaging agents for amyloid plaques.

  DOI：

  10.1021/jm050635e
• 作为产物：
  描述：

  2-羟基-5-溴苯乙酮 在 吡啶 、 potassium hydroxide 作用下， 反应 6.25h， 生成 1-(5-溴-2-羟基苯基)-3-(4-甲氧基苯基)丙烷-1,3-二酮
  参考文献：
  名称：

  钯催化咪唑并[1,2-a]吡啶-黄酮杂化物的简便合成及其抗疟原虫活性的评估

  摘要：

  咪唑并[1,2- a ]吡啶衍生物和6-溴黄酮之间的有效交叉偶联反应已得到很好的建立。该反应通过钯催化的交叉偶联反应进行，以良好至优异的收率提供咪唑并[1,2- a ]吡啶-黄酮杂化物。该方法的主要优点是反应时间短、产率高、底物范围广。使用 SYBR Green I 测定，检查了这些杂合分子对氯喹敏感的 3D7 和氯喹耐药的恶性疟原虫K1 菌株的抗疟原虫活性。化合物9o {IC 50 s (μM) 1.98 3D7 , 1.98 K1 } 和9p {IC50 s (μM) 1.92 3D7 , 5.45 K1 }被发现是该系列中最有效的抗疟原虫化合物。此外，所有这些化合物均被发现对 Vero 细胞无细胞毒性，其 CC 50 s > 100 µM。我们对化合物9o和9p进行了显微镜检查实验，结果对疟疾寄生虫的生长产生了巨大影响。还在野生型Pf -DHFR-TS（恶性疟原虫）的结合位点中检查了

  DOI：

  10.1016/j.molstruc.2023.136282

文献信息

• Microwave-assisted synthesis and antimicrobial activities of flavonoid derivatives
  作者：Sherif B. Abdel Ghani、Louise Weaver、Zidan H. Zidan、Hussein M. Ali、C. William Keevil、Richard C.D. Brown

  DOI：10.1016/j.bmcl.2007.11.081

  日期：2008.1

  Eleven flavonoid derivatives were synthesised using a modified Baker-Venkataraman rearrangement, and subsequent microwave-assisted closure of the heterocyclic ring. All of the synthetic compounds displayed antifungal activity against Aspergillus niger and Fusarium oxysporium, and two of the synthetic flavonoid analogues exhibited significant activity against methicillin-resistant Staphylococcus aureus

  使用修饰的Baker-Venkataraman重排以及随后的微波辅助闭合杂环，合成了11种类黄酮衍生物。所有的合成化合物均对黑曲霉和尖孢镰刀菌具有抗真菌活性，并且两种合成的类黄酮类似物均对耐甲氧西林的金黄色葡萄球菌具有显着的活性。
• 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。
• Composition for diagnosing amyloid-related diseases
  申请人：Nagasaki University

  公开号：US08192717B2

  公开（公告）日：2012-06-05

  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，包括黄酮衍生物、查尔酮衍生物、苯乙烯基香豆素衍生物或香豆素衍生物。这些化合物具有高度的结合特异性，能够与淀粉样β蛋白高度结合，具有高渗透性穿过血脑屏障，且能够迅速从除老年斑外的其他部位消失。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。
• COMPOSITION FOR AMYLOID-ASSOCIATED DISEASE DIAGNOSIS
  申请人：Nagasaki University

  公开号：EP1815872A1

  公开（公告）日：2007-08-08

  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.

  本研究提供了一种用于诊断淀粉样蛋白相关疾病的组合物，该组合物由黄酮衍生物、查尔酮衍生物、苯乙烯基色酮衍生物或香豆素衍生物组成。 这些化合物与淀粉样β蛋白的结合特异性高，对血脑屏障的渗透性高，能够从脑衰老斑块以外的部位迅速消失。 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蛋白相关疾病。
• EP1815872
  申请人：——

  公开号：——

  公开（公告）日：——