3-(azepan-1-yl)propyl 3-phenylpropyl ether

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环庚烷
• 英文名称: 3-(azepan-1-yl)propyl 3-phenylpropyl ether
• 英文别名: FUB 637；1-[3-(3-Phenylpropoxy)propyl]azepane
• 化学式: C₁₈H₂₉NO
• 分子量: 275.434
• InChiKey: OSWRZWGHVFGAON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  环己亚胺 、 1-chloro-3-(3-phenylpropoxy)propane 在 potassium carbonate 、 potassium iodide 作用下， 以 乙醇 为溶剂， 以58%的产率得到3-(azepan-1-yl)propyl 3-phenylpropyl ether
  参考文献：
  名称：

  Influence of imidazole replacement in different structural classes of histamine H3-receptor antagonists

  摘要：

  The reference compounds for histamine H(3)-receptor antagonists carry as a common feature an imidazole moiety substituted in the 4-position. Very recently novel ligands lacking an imidazole ring have been described possessing a N-containing non-aromatic heterocycle instead. In this study we investigated whether imidazole replacement, favourably by a piperidine moiety, is generally applicable to different structural classes of reference compounds, e.g., thioperamide, carboperamide, clobenpropit, FUB 181, ciproxifan, etc. While replacement led to a loss of affinity for many of the compounds, it was successfully applied to some ether derivatives. The piperidine analogues of FB 181 and ciproxifan, 3-(4-chlorophenyl)propyl 3-piperidinopropyl ether hydrogen oxalate (6) and cyclopropyl 4-(3-piperidinopropyloxy)phenyl methanone hydrogen maleate (7), almost maintained in vitro affinities, pK(i) values of 7.8 and 8.4, respectively, and showed high potency in vivo after p.o. administration (ED(50) values of 1.6 and 0.18 mg/kg, respectively). (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0928-0987(01)00106-3

文献信息

• Influence of imidazole replacement in different structural classes of histamine H3-receptor antagonists
  作者：Galina Meier、Joachim Apelt、Ulrich Reichert、Sven Graßmann、Xavier Ligneau、Sigurd Elz、Fabien Leurquin、C.Robin Ganellin、Jean-Charles Schwartz、Walter Schunack、Holger Stark

  DOI：10.1016/s0928-0987(01)00106-3

  日期：2001.6

  The reference compounds for histamine H(3)-receptor antagonists carry as a common feature an imidazole moiety substituted in the 4-position. Very recently novel ligands lacking an imidazole ring have been described possessing a N-containing non-aromatic heterocycle instead. In this study we investigated whether imidazole replacement, favourably by a piperidine moiety, is generally applicable to different structural classes of reference compounds, e.g., thioperamide, carboperamide, clobenpropit, FUB 181, ciproxifan, etc. While replacement led to a loss of affinity for many of the compounds, it was successfully applied to some ether derivatives. The piperidine analogues of FB 181 and ciproxifan, 3-(4-chlorophenyl)propyl 3-piperidinopropyl ether hydrogen oxalate (6) and cyclopropyl 4-(3-piperidinopropyloxy)phenyl methanone hydrogen maleate (7), almost maintained in vitro affinities, pK(i) values of 7.8 and 8.4, respectively, and showed high potency in vivo after p.o. administration (ED(50) values of 1.6 and 0.18 mg/kg, respectively). (C) 2001 Elsevier Science B.V. All rights reserved.