N1-(tert-butoxycarbonyl)-N2-[3-(1H-indol-3-yl)propanoyl]-N1-[3-(1-trityl-1H-imidazol-4-yl)propyl]guanidine | 1146622-63-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N1-(tert-butoxycarbonyl)-N2-[3-(1H-indol-3-yl)propanoyl]-N1-[3-(1-trityl-1H-imidazol-4-yl)propyl]guanidine
• 英文别名: tert-butyl N-[N'-[3-(1H-indol-3-yl)propanoyl]carbamimidoyl]-N-[3-(1-tritylimidazol-4-yl)propyl]carbamate
• CAS: 1146622-63-0
• 化学式: C₄₂H₄₄N₆O₃
• 分子量: 680.85
• InChiKey: SQBRXOWAASFUIW-UHFFFAOYSA-N

物化性质

• 密度：
  1.17±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  51
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-吲哚丙酸 、 3-(1-三苯甲游基-1H-咪唑-4-基)丙烷-1-醇 、 N-(Cbz)-N'-(t-Boc)-guanidine 在 偶氮二甲酸二异丙酯 、 三苯基膦 、 palladium 10% on activated carbon 、 氢气 、 4-二甲氨基吡啶 、 ethylene dichloride hydrochloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 N1-(tert-butoxycarbonyl)-N2-[3-(1H-indol-3-yl)propanoyl]-N3-[3-(1-trityl-1H-imidazol-4-yl)propyl]guanidine 、 N1-(tert-butoxycarbonyl)-N2-[3-(1H-indol-3-yl)propanoyl]-N1-[3-(1-trityl-1H-imidazol-4-yl)propyl]guanidine
  参考文献：
  名称：

  N^G-Acylated Imidazolylpropylguanidines as Potent Histamine H₄ Receptor Agonists: Selectivity by Variation of the N^G-Substituent

  摘要：

  3-(1H-Imidazol-4-yl)propylguanidine (SK&F 91486, 4) was identified as a potent partial agonist at the human histamine H-3 receptor (hH(3)R) and human histamine H-4 receptor (hH(4)R). With the aim to increase selectivity for the hH4R, the guanidine group in 4 was acylated. N-1-Acetyl-N-2-[3-(1H-imidazol-4-yl)propyl]guanidine (UR-PI288, 13) was a potent full agonist at the hH(4)R (pEC(50) = 8.31; alpha = 1.00), possessing more than 1000- and 100-fold selectivity relative to the hH(1)R and hH(2)R, respectively, and possessing only low intrinsic activity (alpha = 0.27) at the hH(3)R.

  DOI：

  10.1021/jm9000693

文献信息

• <i>N</i>^G-Acylated Imidazolylpropylguanidines as Potent Histamine H₄ Receptor Agonists: Selectivity by Variation of the <i>N</i>^G-Substituent
  作者：Patrick Igel、Erich Schneider、David Schnell、Sigurd Elz、Roland Seifert、Armin Buschauer

  DOI：10.1021/jm9000693

  日期：2009.4.23

  3-(1H-Imidazol-4-yl)propylguanidine (SK&F 91486, 4) was identified as a potent partial agonist at the human histamine H-3 receptor (hH(3)R) and human histamine H-4 receptor (hH(4)R). With the aim to increase selectivity for the hH4R, the guanidine group in 4 was acylated. N-1-Acetyl-N-2-[3-(1H-imidazol-4-yl)propyl]guanidine (UR-PI288, 13) was a potent full agonist at the hH(4)R (pEC(50) = 8.31; alpha = 1.00), possessing more than 1000- and 100-fold selectivity relative to the hH(1)R and hH(2)R, respectively, and possessing only low intrinsic activity (alpha = 0.27) at the hH(3)R.