N-(3-(1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-yl)phenyl)-3-(1,3-dioxoisoindolin-2-yl)propanamide | 1416149-72-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(3-(1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-yl)phenyl)-3-(1,3-dioxoisoindolin-2-yl)propanamide
• 英文别名: N-[3-[1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3H-2-benzofuran-5-yl]phenyl]-3-(1,3-dioxoisoindol-2-yl)propanamide
• CAS: 1416149-72-8
• 化学式: C₃₆H₃₄FN₃O₄
• 分子量: 591.682
• InChiKey: SIXMISVKFPDGMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  44
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  79
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(3-(1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-yl)phenyl)-3-(1,3-dioxoisoindolin-2-yl)propanamide 在 乙醇 、 肼 作用下， 反应 5.0h， 以51%的产率得到3-amino-N-(3-(1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-yl)phenyl)propanamide
  参考文献：
  名称：

  A rhodamine-labeled citalopram analogue as a high-affinity fluorescent probe for the serotonin transporter

  摘要：

  A novel fluorescent ligand was synthesized as a high-affinity, high specificity probe for visualizing the serotonin transporter (SERT). The rhodamine fluorophore was extended from an aniline substitution on the 5-position of the dihydroisobenzofuran ring of citalopram (2, 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile), using an ethylamino linker. The resulting rhodamine-labeled ligand 8 inhibited [H-3]5-HT uptake in COS-7 cells (K-i = 225 nM) with similar potency to the tropane-based JHC 1-064 (1), but with higher specificity towards the SERT relative to the transporters for dopamine and norepinephrine. Visualization of the SERT with compound 8 was demonstrated by confocal microscopy in HEK293 cells stably expressing EGFP-SERT. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2012.10.089
• 作为产物：
  描述：

  3-(N-苯二甲酰亚氨基)丙酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 N-(3-(1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-yl)phenyl)-3-(1,3-dioxoisoindolin-2-yl)propanamide
  参考文献：
  名称：

  A rhodamine-labeled citalopram analogue as a high-affinity fluorescent probe for the serotonin transporter

  摘要：

  A novel fluorescent ligand was synthesized as a high-affinity, high specificity probe for visualizing the serotonin transporter (SERT). The rhodamine fluorophore was extended from an aniline substitution on the 5-position of the dihydroisobenzofuran ring of citalopram (2, 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile), using an ethylamino linker. The resulting rhodamine-labeled ligand 8 inhibited [H-3]5-HT uptake in COS-7 cells (K-i = 225 nM) with similar potency to the tropane-based JHC 1-064 (1), but with higher specificity towards the SERT relative to the transporters for dopamine and norepinephrine. Visualization of the SERT with compound 8 was demonstrated by confocal microscopy in HEK293 cells stably expressing EGFP-SERT. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2012.10.089