6-bromo-3-(4-(dimethylamino)phenyl)-2H-chromen-2-one | 887647-17-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 6-bromo-3-(4-(dimethylamino)phenyl)-2H-chromen-2-one
• 英文别名: 6-bromo-3-(4-dimethylaminophenyl)coumarin；6-Bromo-3-[4-(dimethylamino)phenyl]chromen-2-one；6-bromo-3-[4-(dimethylamino)phenyl]chromen-2-one
• CAS: 887647-17-8
• 化学式: C₁₇H₁₄BrNO₂
• 分子量: 344.208
• InChiKey: CJFYYRPTYDWCBF-UHFFFAOYSA-N

物化性质

• 沸点：
  497.8±45.0 °C(Predicted)
• 密度：
  1.474±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-bromo-3-(4-(dimethylamino)phenyl)-2H-chromen-2-one 、 六正丁基二锡 在 四(三苯基膦)钯 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以29%的产率得到3-(4-(dimethylamino)phenyl)-6-(tributylstannyl)-2H-chromen-2-one
  参考文献：
  名称：

  Synthesis and biological evaluation of radioiodinated 3-phenylcoumarin derivatives targeting myelin in multiple sclerosis

  摘要：

  Myelin is a lipid multilayer involved in the rate of nerve transmission, and its loss is a pathological feature of multiple sclerosis in brains. Since in vivo imaging of myelin may be useful for drug development, early diagnosis, and monitoring the disease stage, we designed, synthesized, and evaluated eight novel radioiodinated 3-phenylcoumarin derivatives as imaging probes targeting myelin. In the biodistribution study using normal mice, all compounds displayed sufficient brain uptake, ranging from 2.5 to 5.0% ID/g, at 2 min postinjection. On ex vivo autoradiography, [¹²⁵I]18 and [¹²⁵I]21, which have a dimethylamino group, showed high binding affinity for myelin in the normal mouse brain. In addition, the radioactivity accumulation of [¹²⁵I]21 in the white matter of the spinal cord in the experimental autoimmune encephalomyelitis mice was lower than that in naive mice. These results suggest that [¹²³I]21 shows potential as a single photon emission computed tomography probe targeting myelin.

  DOI：

  10.1016/j.bmcl.2020.127562
• 作为产物：
  描述：

  聚合甲醛 、 6-bromo-3-(4-aminophenyl)coumarin 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以37.2%的产率得到6-bromo-3-(4-(dimethylamino)phenyl)-2H-chromen-2-one
  参考文献：
  名称：

  Synthesis and biological evaluation of radioiodinated 3-phenylcoumarin derivatives targeting myelin in multiple sclerosis

  摘要：

  Myelin is a lipid multilayer involved in the rate of nerve transmission, and its loss is a pathological feature of multiple sclerosis in brains. Since in vivo imaging of myelin may be useful for drug development, early diagnosis, and monitoring the disease stage, we designed, synthesized, and evaluated eight novel radioiodinated 3-phenylcoumarin derivatives as imaging probes targeting myelin. In the biodistribution study using normal mice, all compounds displayed sufficient brain uptake, ranging from 2.5 to 5.0% ID/g, at 2 min postinjection. On ex vivo autoradiography, [¹²⁵I]18 and [¹²⁵I]21, which have a dimethylamino group, showed high binding affinity for myelin in the normal mouse brain. In addition, the radioactivity accumulation of [¹²⁵I]21 in the white matter of the spinal cord in the experimental autoimmune encephalomyelitis mice was lower than that in naive mice. These results suggest that [¹²³I]21 shows potential as a single photon emission computed tomography probe targeting myelin.

  DOI：

  10.1016/j.bmcl.2020.127562

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。
• 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：——
• US8192717B2
  申请人：——

  公开号：US8192717B2

  公开（公告）日：2012-06-05
• Synthesis and biological evaluation of radioiodinated 3-phenylcoumarin derivatives targeting myelin in multiple sclerosis
  作者：Hiroyuki Watanabe、Shiori Sakai、Shimpei Iikuni、Yoichi Shimizu、Hisashi Shirakawa、Shuji Kaneko、Masahiro Ono

  DOI：10.1016/j.bmcl.2020.127562

  日期：2020.12

  Myelin is a lipid multilayer involved in the rate of nerve transmission, and its loss is a pathological feature of multiple sclerosis in brains. Since in vivo imaging of myelin may be useful for drug development, early diagnosis, and monitoring the disease stage, we designed, synthesized, and evaluated eight novel radioiodinated 3-phenylcoumarin derivatives as imaging probes targeting myelin. In the biodistribution study using normal mice, all compounds displayed sufficient brain uptake, ranging from 2.5 to 5.0% ID/g, at 2 min postinjection. On ex vivo autoradiography, [¹²⁵I]18 and [¹²⁵I]21, which have a dimethylamino group, showed high binding affinity for myelin in the normal mouse brain. In addition, the radioactivity accumulation of [¹²⁵I]21 in the white matter of the spinal cord in the experimental autoimmune encephalomyelitis mice was lower than that in naive mice. These results suggest that [¹²³I]21 shows potential as a single photon emission computed tomography probe targeting myelin.