3-[1H-indole-2-carbonyl(methyl)amino]propanoic acid | 1146622-61-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-[1H-indole-2-carbonyl(methyl)amino]propanoic acid
• CAS: 1146622-61-8
• 化学式: C₁₃H₁₄N₂O₃
• 分子量: 246.266
• InChiKey: BZXSCZBDXCQSFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  73.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  三氟乙酸 、 3-(1-三苯甲游基-1H-咪唑-4-基)丙烷-1-醇 、 N-(Cbz)-N'-(t-Boc)-guanidine 、 3-[1H-indole-2-carbonyl(methyl)amino]propanoic acid 在 偶氮二甲酸二异丙酯 、 三苯基膦 、 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 以64%的产率得到N1-[3-(1H-imidazol-4-yl)propyl]-N2-[3-(N-methyl-1H-indole-2-carbonylamino)propanoyl]guanidinium ditrifluoroacetate
  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
• 作为产物：
  描述：

  methyl 3-[1H-indole-2-carbonyl(methyl)amino]propanoate 在 lithium hydroxide monohydrate 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以90%的产率得到3-[1H-indole-2-carbonyl(methyl)amino]propanoic acid
  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