(E)-3-(4-(dimethylamino)phenyl)-1-(4-iodophenyl)-2-propen-1-one

• 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: (E)-3-(4-(dimethylamino)phenyl)-1-(4-iodophenyl)-2-propen-1-one
• 英文别名: 4-dimethylamino-4'-iodo-chalcone；DMIC；(E)-3-(4-(dimethylamino)phenyl)-1-(4-iodophenyl)propan-2-en-1-one；(E)-3-(4-(dimethylamino)phenyl)-1-(4-iodophenyl)prop-2-en-1-one；3-[4-(Dimethylamino)phenyl]-1-(4-iodophenyl)-2-propen-1-one；(E)-3-[4-(dimethylamino)phenyl]-1-(4-iodophenyl)prop-2-en-1-one
• 化学式: C₁₇H₁₆INO
• 分子量: 377.225
• InChiKey: OZBWMKUXDHFFFT-LFYBBSHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-(dimethylamino)phenyl)-1-(4-iodophenyl)-2-propen-1-one 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 Cu(OTf)2(py)4 、 potassium acetate 、 potassium carbonate 、 4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷 、 氢氟酸 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.33h， 生成
  参考文献：
  名称：

  Conversion of iodine to fluorine-18 based on iodinated chalcone and evaluation for β-amyloid PET imaging

  摘要：

  In the amyloid cascade hypothesis, beta-amyloid (A beta) plaques is one of the major pathological biomarkers in the Alzheimer's disease (AD) brain. We report the synthesis and evaluation of novel radiofluorinated chalcones, [F-18] 4-dimethylamino-4'-fluoro-chalcone ([F-18] DMFC) and [F-18] 4'-fluoro-4-methylamino-chalcone ([F-18] FMC), as A beta imaging probes. The conversion of iodine directly introduced to the chalcone backbone into fluorine was successfully carried out by F-18-labeling via the corresponding boronate precursors, achieving the direct introduction of fluorine-18 into the chalcone backbone to prepare [F-18] DMFC and [F-18] FMC. In a biodistribution study using normal mice, [F-18] DMFC and [F-18] FMC showed a higher initial uptake (4.43 and 5.47% ID/g at 2 min postinjection, respectively) into and more rapid clearance (0.52 and 0.66% ID/g at 30 min postinjection, respectively) from the brain than a Food and Drug Administration (FDA)-approved A beta imaging agent ([F-18] Florbetapir), meaning the improvement of the probability of detecting A beta plaques and the reduction of non-specific binding in the brain. In the in vitro binding studies using aggregates of recombinant A beta peptides, [F-18] DMFC and [F-18] FMC showed high binding affinity to recombinant A beta aggregates at the K-d values of 4.47 and 6.50 nM, respectively. In the in vitro autoradiography (ARG) experiment with AD brain sections, [F-18] DMFC and [F-18] FMC markedly accumulated only in a region with abundant A beta plaques, indicating that they clearly recognized human A beta plaques in vitro. These encouraging results suggest that [F-18] DMFC and [F-18] FMC may be promising PET probes for the detection of an amyloid pathology and the early diagnosis of AD with marked accuracy. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2018.05.001
• 作为产物：
  描述：

  (E)-1-(4-(tributylstannyl)phenyl)-3-(4-(dimethylamino)phenyl)prop-2-en-1-one 在 碘 作用下， 以 氯仿 为溶剂， 反应 0.5h， 以46.6%的产率得到(E)-3-(4-(dimethylamino)phenyl)-1-(4-iodophenyl)-2-propen-1-one
  参考文献：
  名称：

  COMPOSITION FOR DIAGNOSING AMYLOID-RELATED DISEASE

  摘要：

  提供了一种化合物组合物，其由一般式（I）表示的化合物组成，其中R1代表5-碘噻吩-2-基基团或类似物，R2代表4-二甲氨基苯基团或类似物。该组合物对于诊断与淀粉样蛋白相关的疾病，如阿尔茨海默病，具有高结合特异性，高透过血脑屏障的渗透性，以及在大脑老年斑以外部位迅速被排除的特性。

  公开号：

  EP2030635A1

文献信息

• COMPOSITION FOR DIAGNOSIS OF AMYLOID-RELATED DISEASE
  申请人：Nakayama Morio

  公开号：US20100278733A1

  公开（公告）日：2010-11-04

  There is provided a composition comprising a compound represented by general formula (I), wherein R l represents a 5-iodothiophen-2-yl group or the like, and R 2 represents a 4-dimethylaminophenyl group or the like. This composition is useful for diagnosis of an amyloid-related disease such as Alzheimer's disease because the compound has high binding specificity to amyloid β protein, high permeability through the blood-brain barrier, and a property of being rapidly eliminated from sites other than senile plaques in the brain.

  提供了一种化合物组合物，其由一般式(I)所代表的化合物组成，其中R1代表5-碘噻吩-2-基基团或类似物，R2代表4-二甲氨基苯基基团或类似物。该组合物对于诊断与淀粉样蛋白相关的疾病，如阿尔茨海默病，具有高结合特异性，高透过血脑屏障的渗透性，以及在大脑老年斑以外的部位迅速被排除的特性。
• COMPOSITION FOR DIAGNOSING AMYLOID-RELATED DISEASE
  申请人：Nagasaki University

  公开号：EP2030635A1

  公开（公告）日：2009-03-04

  There is provided a composition comprising a compound represented by general formula (I), wherein R1 represents a 5-iodothiophen-2-yl group or the like, and R2 represents a 4-dimethylaminophenyl group or the like. This composition is useful for diagnosis of an amyloid-related disease such as Alzheimer's disease because the compound has high binding specificity to amyloid β protein, high permeability through the blood-brain barrier, and a property of being rapidly eliminated from sites other than senile plaques in the brain.

  提供了一种化合物组合物，其由一般式（I）表示的化合物组成，其中R1代表5-碘噻吩-2-基基团或类似物，R2代表4-二甲氨基苯基团或类似物。该组合物对于诊断与淀粉样蛋白相关的疾病，如阿尔茨海默病，具有高结合特异性，高透过血脑屏障的渗透性，以及在大脑老年斑以外部位迅速被排除的特性。
• RADIOACTIVE IODINE LABELED ORGANIC COMPOUND OR SALT THEREOF
  申请人：Saji Hideo

  公开号：US20120330024A1

  公开（公告）日：2012-12-27

  The present invention is a compound represented by the following formula (1) or a salt thereof. Furthermore, the present invention is an imaging agent used for imaging a tau protein, the imaging agent containing a compound represented by the formula (1) below or a salt thereof. In the formula (1), R 3 is a radioactive iodine.

  本发明是由以下式（1）表示的化合物或其盐。此外，本发明是用于成像tau蛋白的成像剂，该成像剂含有以下式（1）表示的化合物或其盐。在式（1）中，R3是放射性碘。
• 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 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。