2-[3-(diethylamino)-6-diethylazaniumylidenexanthen-9-yl]-5-[[6-[[3-[3-[1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3H-2-benzofuran-5-yl]anilino]-3-oxopropyl]amino]-6-oxohexyl]sulfamoyl]benzenesulfonate | 1416149-74-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-[3-(diethylamino)-6-diethylazaniumylidenexanthen-9-yl]-5-[[6-[[3-[3-[1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3H-2-benzofuran-5-yl]anilino]-3-oxopropyl]amino]-6-oxohexyl]sulfamoyl]benzenesulfonate
• CAS: 1416149-74-0
• 化学式: C₆₁H₇₁FN₆O₉S₂
• 分子量: 1115.4
• InChiKey: YCPGWXQYWPBVKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  79
• 可旋转键数：
  24
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  206
• 氢给体数：
  3
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  rhodamine red N-hydroxysuccinimide ester 、 3-amino-N-(3-(1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-yl)phenyl)propanamide 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以90%的产率得到2-[3-(diethylamino)-6-diethylazaniumylidenexanthen-9-yl]-5-[[6-[[3-[3-[1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3H-2-benzofuran-5-yl]anilino]-3-oxopropyl]amino]-6-oxohexyl]sulfamoyl]benzenesulfonate
  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