3-(benzo[d][1,3]dioxol-5-yl)-6-bromo-2H-chromen-2-one

• 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-(benzo[d][1,3]dioxol-5-yl)-6-bromo-2H-chromen-2-one
• 英文别名: 3-(1,3-benzodioxol-5-yl)-6-bromochromen-2-one
• 化学式: C₁₆H₉BrO₄
• 分子量: 345.149
• InChiKey: UQOBAOUHFGPWIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  六正丁基二锡 、 3-(benzo[d][1,3]dioxol-5-yl)-6-bromo-2H-chromen-2-one 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13.2%的产率得到3-(benzo[d][1,3]dioxol-5-yl)-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：

  胡椒乙酸 、 5-溴水杨醛 在 potassium acetate 、 乙酸酐 作用下， 以73.9%的产率得到3-(benzo[d][1,3]dioxol-5-yl)-6-bromo-2H-chromen-2-one
  参考文献：
  名称：

  Synthesis of Analogues of Natural Coumarins and Coumarinolignans

  摘要：

  通过改进的方法合成了具有 1,3-苯并二恶茂、1,4-苯并二恶烷和 1,5-苯并二恶烷分子的 3-芳基-4H-香豆素。

  DOI：

  10.1007/s11171-005-0040-6

文献信息

• Synthetic and modified isoflavonoids. IX. Synthesis of benzodioxolane and benzodioxane analogs of 3-arylcoumarins
  作者：A. Aitmambetov、V. P. Khilya

  DOI：10.1007/bf00630008

  日期：1994.3
• 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.
• Synthesis of Analogues of Natural Coumarins and Coumarinolignans
  作者：G. O. Ismailova

  DOI：10.1007/s11171-005-0040-6

  日期：2005.5

  3-Aryl-4H-coumarins with the 1,3-benzodioxol, 1,4-benzodioxane, and 1,5-benzodioxepane moieties were synthesized by modified methods.

  通过改进的方法合成了具有 1,3-苯并二恶茂、1,4-苯并二恶烷和 1,5-苯并二恶烷分子的 3-芳基-4H-香豆素。