methyl 4-(1H-indole-2-carboxamido)butanoate | 1146622-77-6

• 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: methyl 4-(1H-indole-2-carboxamido)butanoate
• 英文别名: methyl 4-(1H-indole-2-carbonylamino)butanoate
• CAS: 1146622-77-6
• 化学式: C₁₄H₁₆N₂O₃
• 分子量: 260.293
• InChiKey: FDMBCPRVZOBAHV-UHFFFAOYSA-N

物化性质

• 沸点：
  533.8±30.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  71.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 4-(1H-indole-2-carboxamido)butanoate 在 lithium hydroxide monohydrate 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以58%的产率得到4-(1H-indole-2-carboxamido)butanoic 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
• 作为产物：
  描述：

  吲哚-2-羧酸 、 4-氨基丁酸甲酯盐酸盐 在 4-二甲氨基吡啶 、 ethylene dichloride hydrochloride 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以63%的产率得到methyl 4-(1H-indole-2-carboxamido)butanoate
  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.