(1S,3R)-N-((5-(4-chlorophenyl)-1-isopropyl-4-(2-methoxyethyl)-1H-imidazol-2-yl)methyl)-3-fluorocyclopentanamine | 1187842-59-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (1S,3R)-N-((5-(4-chlorophenyl)-1-isopropyl-4-(2-methoxyethyl)-1H-imidazol-2-yl)methyl)-3-fluorocyclopentanamine
• 英文别名: (1S,3R)-N-[[5-(4-chlorophenyl)-4-(2-methoxyethyl)-1-propan-2-ylimidazol-2-yl]methyl]-3-fluorocyclopentan-1-amine
• CAS: 1187842-59-6
• 化学式: C₂₁H₂₉ClFN₃O
• 分子量: 393.932
• InChiKey: ZTCQDGJUOYNCFZ-MSOLQXFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  39.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 三氟乙酸 作用下， 以48%的产率得到(1S,3R)-N-((5-(4-chlorophenyl)-1-isopropyl-4-(2-methoxyethyl)-1H-imidazol-2-yl)methyl)-3-fluorocyclopentanamine
  参考文献：
  名称：

  Synthesis and biological evaluation of imidazole derivatives as novel NOP/ORL1 receptor antagonists: Exploration and optimization of alternative pyrazole structure

  摘要：

  Nonpeptidic small-molecule NOP/ORL1 receptor antagonists with an imidazole scaffold were designed and synthesized to investigate alternatives to the pyrazole analog. Systematic modification of the original pyrazole lead [Kobayashi et al., Bioorg. Med. Chem. Lett. 2009, 19, 3627; Kobayashi et al., Bioorg. Med. Chem. Lett., in press] to change the heterocyclic core, substituted side chain, and pendant functional group demonstrated that examining the structure-activity relationship for novel templates allowed the identification of potent, fully substituted 4-aminomethyl-1H-imidazole and 2-aminomethyl-1H-imidazole. These compounds exhibited excellent potency for ORL1 receptor with minimal P-gp efflux and/or reduced hERG affinity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.06.095