2-[4-({3-[(tert-butoxycarbonyl)amino]propanoyl}amino)piperidino]ethyl 4-amino-5-chloro-2-methoxybenzoate | 868599-24-0

• 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: 2-[4-({3-[(tert-butoxycarbonyl)amino]propanoyl}amino)piperidino]ethyl 4-amino-5-chloro-2-methoxybenzoate
• 英文别名: 2-[4-[3-[(2-Methylpropan-2-yl)oxycarbonylamino]propanoylamino]piperidin-1-yl]ethyl 4-amino-5-chloro-2-methoxybenzoate
• CAS: 868599-24-0
• 化学式: C₂₃H₃₅ClN₄O₆
• 分子量: 499.007
• InChiKey: AQEPHNFWUTWWSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  132
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-[4-({3-[(tert-butoxycarbonyl)amino]propanoyl}amino)piperidino]ethyl 4-amino-5-chloro-2-methoxybenzoate 在 盐酸 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 2-[4-[[3-[[1-[2-(4-Amino-5-chloro-2-methoxybenzoyl)oxyethyl]piperidin-4-yl]amino]-3-oxopropyl]carbamoyl]piperidin-1-yl]ethyl 4-amino-5-chloro-2-methoxybenzoate
  参考文献：
  名称：

  Design and Synthesis of Specific Probes for Human 5-HT₄ Receptor Dimerization Studies

  摘要：

  Recently, human 5-HT4 receptors have been demonstrated to form constitutive dimers in living cells. To evaluate the role of dimerization on the 5-HT4 receptor function, we investigated the conception and the synthesis of bivalent molecules able to influence the dimerization process. Their conception is based on a model of the 5-HT4 receptor dimer derived from protein/protein docking experiments. These bivalent ligands are constituted by two ML10302 units, a specific 5-HT4 ligand, linked through a spacer of different sizes and natures. These synthesized bivalent ligands were evaluated in binding assays and cyclic AMP production on the 5-HT4(e/g) receptor isoform stably transfected in C6 glial cells. Our data showed that bivalent ligands conserved a similar affinity compared to the basal ML10302 unit. Nevertheless, according to the nature and the size of the spacer, the pharmacological profile of ML10302 is more or less conserved. In view of the interest of bivalent ligands for investigating the GPCR dimerization process, these 5-HT4 specific bivalent ligands constitute valuable pharmacological tools for the study of 5-HT4 receptor dimerization.

  DOI：

  10.1021/jm050234z
• 作为产物：
  描述：

  Boc-beta-丙氨酸 、 2-(4-aminopiperidin-1-yl)ethyl 4-amino-5-chloro-2-methoxybenzoate 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以31%的产率得到2-[4-({3-[(tert-butoxycarbonyl)amino]propanoyl}amino)piperidino]ethyl 4-amino-5-chloro-2-methoxybenzoate
  参考文献：
  名称：

  Design and Synthesis of Specific Probes for Human 5-HT₄ Receptor Dimerization Studies

  摘要：

  Recently, human 5-HT4 receptors have been demonstrated to form constitutive dimers in living cells. To evaluate the role of dimerization on the 5-HT4 receptor function, we investigated the conception and the synthesis of bivalent molecules able to influence the dimerization process. Their conception is based on a model of the 5-HT4 receptor dimer derived from protein/protein docking experiments. These bivalent ligands are constituted by two ML10302 units, a specific 5-HT4 ligand, linked through a spacer of different sizes and natures. These synthesized bivalent ligands were evaluated in binding assays and cyclic AMP production on the 5-HT4(e/g) receptor isoform stably transfected in C6 glial cells. Our data showed that bivalent ligands conserved a similar affinity compared to the basal ML10302 unit. Nevertheless, according to the nature and the size of the spacer, the pharmacological profile of ML10302 is more or less conserved. In view of the interest of bivalent ligands for investigating the GPCR dimerization process, these 5-HT4 specific bivalent ligands constitute valuable pharmacological tools for the study of 5-HT4 receptor dimerization.

  DOI：

  10.1021/jm050234z