5-(1H-imidazol-4-yl)pentanoic acid ethyl ester | 887276-81-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(1H-imidazol-4-yl)pentanoic acid ethyl ester
• 英文别名: ethyl 5-(1H-imidazol-5-yl)pentanoate
• CAS: 887276-81-5
• 化学式: C₁₀H₁₆N₂O₂
• 分子量: 196.249
• InChiKey: LFMRVIXDLLIOMH-UHFFFAOYSA-N

物化性质

• 沸点：
  367.0±25.0 °C(Predicted)
• 密度：
  1.091±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(1H-imidazol-4-yl)pentanoic acid ethyl ester 在 lithium aluminium tetrahydride 、 草酰氯 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 0.42h， 生成 ethyl-[5-(1-trityl-1H-imidazol-4-yl)pentyl]amine
  参考文献：
  名称：

  A Chemical Switch for the Modulation of the Functional Activity of Higher Homologues of Histamine on the Human Histamine H₃ Receptor:  Effect of Various Substitutions at the Primary Amino Function

  摘要：

  In ail effort to establish the structural requirements for agonism, neutral antagonism, and inverse agonism at the human histamine H-3 receptor (H3R) we have prepared a series of higher homologues of histamine in which the terminal nitrogen of the side chain has been either mono- or disubstituted with several aliphatic, alicyclic, and aromatic moieties or incorporated in cyclic systems. The novel ligands have been pharmacologically investigated in vitro for their affinities on the human H3R and H4R subtypes by radioligand displacement experiments and for their intrinsic H3R activities via a CRE-mediated P-galactosidase reporter gene assay. Subtle changes of the substitution pattern at the side chain nitrogen alter enormously the pharmacological activity of the ligands, resulting in a series of compounds with a wide spectrum of pharmacological activities. Among the several neutral H3R antagonists identified within this series, compounds 2b and 2h display an H3R affinity in the low nanomolar concentration range (pK(i) values of 8.1 and 8.4, respectively). A very potent and selective H3R agonist (1l, pEC(50) 8.9, alpha = 0.94) and a very potent, though not highly selective, H3R inverse agonist (2k, pIC(50) = 8-9, alpha -0.97) have been identified as well.

  DOI：

  10.1021/jm0504353
• 作为产物：
  描述：

  6-羟基己酸甲酯 在 草酰氯 、 氰化钠 、 氨 、 二甲基亚砜 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 52.5h， 生成 5-(1H-imidazol-4-yl)pentanoic acid ethyl ester
  参考文献：
  名称：

  A Chemical Switch for the Modulation of the Functional Activity of Higher Homologues of Histamine on the Human Histamine H₃ Receptor:  Effect of Various Substitutions at the Primary Amino Function

  摘要：

  In ail effort to establish the structural requirements for agonism, neutral antagonism, and inverse agonism at the human histamine H-3 receptor (H3R) we have prepared a series of higher homologues of histamine in which the terminal nitrogen of the side chain has been either mono- or disubstituted with several aliphatic, alicyclic, and aromatic moieties or incorporated in cyclic systems. The novel ligands have been pharmacologically investigated in vitro for their affinities on the human H3R and H4R subtypes by radioligand displacement experiments and for their intrinsic H3R activities via a CRE-mediated P-galactosidase reporter gene assay. Subtle changes of the substitution pattern at the side chain nitrogen alter enormously the pharmacological activity of the ligands, resulting in a series of compounds with a wide spectrum of pharmacological activities. Among the several neutral H3R antagonists identified within this series, compounds 2b and 2h display an H3R affinity in the low nanomolar concentration range (pK(i) values of 8.1 and 8.4, respectively). A very potent and selective H3R agonist (1l, pEC(50) 8.9, alpha = 0.94) and a very potent, though not highly selective, H3R inverse agonist (2k, pIC(50) = 8-9, alpha -0.97) have been identified as well.

  DOI：

  10.1021/jm0504353