3-(4-(dimethylamino)phenyl)-6-(tributylstannyl)-2H-chromen-2-one | 887647-20-3

• 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: 3-(4-(dimethylamino)phenyl)-6-(tributylstannyl)-2H-chromen-2-one
• 英文别名: 6-(tributylstannyl)-3-(4-dimethylaminophenyl)coumarin；3-[4-(Dimethylamino)phenyl]-6-tributylstannylchromen-2-one；3-[4-(dimethylamino)phenyl]-6-tributylstannylchromen-2-one
• CAS: 887647-20-3
• 化学式: C₂₉H₄₁NO₂Sn
• 分子量: 554.36
• InChiKey: DGSYBGODGWVYSL-UHFFFAOYSA-N

物化性质

• 沸点：
  601.4±65.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.58
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 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：

  3-(4-(dimethylamino)phenyl)-6-(tributylstannyl)-2H-chromen-2-one 在 碘 、 sodium hydrogensulfite 作用下， 以 氯仿 、 水 为溶剂， 反应 0.17h， 以95%的产率得到3-(4-(dimethylamino)phenyl)-6-iodo-2H-chromen-2-one
  参考文献：
  名称：

  EP1815872

  摘要：

  公开号：
• 作为产物：
  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

文献信息

• EP1815872
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.