tert-butyl 4-(5-{[(5-chloro-3-methyl-1-benzothien-2-yl)sulfonyl][8-({[5-(dimethylamino)-1-naphthyl]sulfonyl}amino)octyl]amino}-2-methoxyphenyl)piperazine-1-carboxylate | 1246948-60-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: tert-butyl 4-(5-{[(5-chloro-3-methyl-1-benzothien-2-yl)sulfonyl][8-({[5-(dimethylamino)-1-naphthyl]sulfonyl}amino)octyl]amino}-2-methoxyphenyl)piperazine-1-carboxylate
• 英文别名: Tert-butyl 4-[5-[(5-chloro-3-methyl-1-benzothiophen-2-yl)sulfonyl-[8-[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]octyl]amino]-2-methoxyphenyl]piperazine-1-carboxylate
• CAS: 1246948-60-6
• 化学式: C₄₅H₅₈ClN₅O₇S₃
• 分子量: 912.636
• InChiKey: MDHRPZZBZXUDEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  61
• 可旋转键数：
  19
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  174
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-(5-{[(5-chloro-3-methyl-1-benzothien-2-yl)sulfonyl][8-({[5-(dimethylamino)-1-naphthyl]sulfonyl}amino)octyl]amino}-2-methoxyphenyl)piperazine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以97%的产率得到5-chloro-N-[8-({[5-(dimethylamino)-1-naphthyl]sulfonyl}amino)-octyl]-N-(4-methoxy-3-piperazin-1-ylphenyl)-3-methyl-1-benzothiophene-2-sulfonamide
  参考文献：
  名称：

  Development of Molecular Probes for the Human 5-HT₆ Receptor

  摘要：

  In this work we report the synthesis of a set of labeled ligands targeting the human 5-HT6, receptor (h5-HT6R). Among the synthesized compounds, fluorescent probe 10 (K-i = 175 nM and Phi(f) = 0.21 and biotinylated derivative 15 (K-i = 90 nM) deserve special attention because they enable direct observation of the h5-HT6R in cells. Thus, they represent the first molecular probes for 5-HT6R visualization. These results are the starting point for introducing a variety of tags in these or other 5-HT6R ligand scaffolds aimed at the development of optimized probes with tailored profiles in terms of fluorescence, affinity, or selectivity.

  DOI：

  10.1021/jm1007177
• 作为产物：
  描述：

  tert-butyl 4-(5-{(8-aminooctyl)[(5-chloro-3-methyl-1-benzothien-2-yl)sulfonyl]amino}-2-methoxyphenyl)piperazine-1-carboxylate 、 丹酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以152 mg的产率得到tert-butyl 4-(5-{[(5-chloro-3-methyl-1-benzothien-2-yl)sulfonyl][8-({[5-(dimethylamino)-1-naphthyl]sulfonyl}amino)octyl]amino}-2-methoxyphenyl)piperazine-1-carboxylate
  参考文献：
  名称：

  Development of Molecular Probes for the Human 5-HT₆ Receptor

  摘要：

  In this work we report the synthesis of a set of labeled ligands targeting the human 5-HT6, receptor (h5-HT6R). Among the synthesized compounds, fluorescent probe 10 (K-i = 175 nM and Phi(f) = 0.21 and biotinylated derivative 15 (K-i = 90 nM) deserve special attention because they enable direct observation of the h5-HT6R in cells. Thus, they represent the first molecular probes for 5-HT6R visualization. These results are the starting point for introducing a variety of tags in these or other 5-HT6R ligand scaffolds aimed at the development of optimized probes with tailored profiles in terms of fluorescence, affinity, or selectivity.

  DOI：

  10.1021/jm1007177

文献信息

• Development of Molecular Probes for the Human 5-HT₆ Receptor
  作者：Henar Vázquez-Villa、Juan A. González-Vera、Bellinda Benhamú、Alma Viso、Roberto Fernández de la Pradilla、Elena Junquera、Emilio Aicart、María L. López-Rodríguez、Silvia Ortega-Gutiérrez

  DOI：10.1021/jm1007177

  日期：2010.10.14

  In this work we report the synthesis of a set of labeled ligands targeting the human 5-HT6, receptor (h5-HT6R). Among the synthesized compounds, fluorescent probe 10 (K-i = 175 nM and Phi(f) = 0.21 and biotinylated derivative 15 (K-i = 90 nM) deserve special attention because they enable direct observation of the h5-HT6R in cells. Thus, they represent the first molecular probes for 5-HT6R visualization. These results are the starting point for introducing a variety of tags in these or other 5-HT6R ligand scaffolds aimed at the development of optimized probes with tailored profiles in terms of fluorescence, affinity, or selectivity.