1-(3'-benzyloxycarbonylaminophenyl)-4-methylpiperazine | 378759-37-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-(3'-benzyloxycarbonylaminophenyl)-4-methylpiperazine
• 英文别名: benzyl N-[3-(4-methylpiperazin-1-yl)phenyl]carbamate
• CAS: 378759-37-6
• 化学式: C₁₉H₂₃N₃O₂
• 分子量: 325.411
• InChiKey: RMNPUYJCNODZDF-UHFFFAOYSA-N

物化性质

• 沸点：
  455.5±45.0 °C(Predicted)
• 密度：
  1.192±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  44.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(3'-benzyloxycarbonylaminophenyl)-4-methylpiperazine 在 氢溴酸 、 溶剂黄146 作用下， 以 乙醚 为溶剂， 反应 12.0h， 生成 4-(3'-aminophenyl)-1,1-dimethylpiperazinium bromide hydrobromide
  参考文献：
  名称：

  Structure−Affinity Relationships of a Unique Nicotinic Ligand:  N-Dimethyl-N⁴-phenylpiperazinium Iodide (DMPP)

  摘要：

  DMPP is a well-known nicotinic agonist that does not fit any proposed pharmacophore for nicotinic binding and represents a unique ligand among the hundreds of nicotinic agonists studied in the past decades. A systematic modulation of the chemical structure of DMPP, aimed to establish its structure-affinity relationships, is reported. The research has allowed to identify molecules such as I Ic, 13c, 14c, and 28c, with affinities for alpha (4)beta (2) receptors in the low nanomolar range, some 2 orders of magnitude lower than the lead compound. The agonistic properties of the most interesting compounds have been assessed by measuring their analgesic activity on mice (hot-plate test). Another result of the research was the identification of DMPP analogues, such as 3a (K-i = 90 nM) and 14b (K-i = 180 nM), that maintain affinity for the central nicotinic receptor when the ammonium function is changed into an aminic one and are therefore possible leads for drug development in neurodegenerative diseases.

  DOI：

  10.1021/jm010901y
• 作为产物：
  描述：

  1-(3-硝基苯基)哌嗪 在 盐酸 、 甲酸 、 tin(ll) chloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 64.0h， 生成 1-(3'-benzyloxycarbonylaminophenyl)-4-methylpiperazine
  参考文献：
  名称：

  Structure−Affinity Relationships of a Unique Nicotinic Ligand:  N-Dimethyl-N⁴-phenylpiperazinium Iodide (DMPP)

  摘要：

  DMPP is a well-known nicotinic agonist that does not fit any proposed pharmacophore for nicotinic binding and represents a unique ligand among the hundreds of nicotinic agonists studied in the past decades. A systematic modulation of the chemical structure of DMPP, aimed to establish its structure-affinity relationships, is reported. The research has allowed to identify molecules such as I Ic, 13c, 14c, and 28c, with affinities for alpha (4)beta (2) receptors in the low nanomolar range, some 2 orders of magnitude lower than the lead compound. The agonistic properties of the most interesting compounds have been assessed by measuring their analgesic activity on mice (hot-plate test). Another result of the research was the identification of DMPP analogues, such as 3a (K-i = 90 nM) and 14b (K-i = 180 nM), that maintain affinity for the central nicotinic receptor when the ammonium function is changed into an aminic one and are therefore possible leads for drug development in neurodegenerative diseases.

  DOI：

  10.1021/jm010901y

文献信息

• Structure−Affinity Relationships of a Unique Nicotinic Ligand:  N-Dimethyl-N⁴-phenylpiperazinium Iodide (DMPP)
  作者：Maria Novella Romanelli、Dina Manetti、Serena Scapecchi、Pier Andrea Borea、Silvia Dei、Alessandro Bartolini、Carla Ghelardini、Fulvio Gualtieri、Luca Guandalini、Katia Varani

  DOI：10.1021/jm010901y

  日期：2001.11.1

  DMPP is a well-known nicotinic agonist that does not fit any proposed pharmacophore for nicotinic binding and represents a unique ligand among the hundreds of nicotinic agonists studied in the past decades. A systematic modulation of the chemical structure of DMPP, aimed to establish its structure-affinity relationships, is reported. The research has allowed to identify molecules such as I Ic, 13c, 14c, and 28c, with affinities for alpha (4)beta (2) receptors in the low nanomolar range, some 2 orders of magnitude lower than the lead compound. The agonistic properties of the most interesting compounds have been assessed by measuring their analgesic activity on mice (hot-plate test). Another result of the research was the identification of DMPP analogues, such as 3a (K-i = 90 nM) and 14b (K-i = 180 nM), that maintain affinity for the central nicotinic receptor when the ammonium function is changed into an aminic one and are therefore possible leads for drug development in neurodegenerative diseases.