2-methyl-3-[4-(4-chlorophenyl) piperazinylmethyl]imidazo-[1,2-a]-pyridine | 1224470-82-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 2-methyl-3-[4-(4-chlorophenyl) piperazinylmethyl]imidazo-[1,2-a]-pyridine
• 英文别名: 2-Methyl-3-[4-(4-chlorophenyl)piperazinylmethyl]imidazo-[1,2-a]-pyridine；3-[[4-(4-chlorophenyl)piperazin-1-yl]methyl]-2-methylimidazo[1,2-a]pyridine
• CAS: 1224470-82-9
• 化学式: C₁₉H₂₁ClN₄
• 分子量: 340.856
• InChiKey: KPTAMQXXLRVOOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(4-氯苯基)哌嗪 、 2-甲基吲哚[1,2-A]吡啶-3-甲醛 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 以45%的产率得到2-methyl-3-[4-(4-chlorophenyl) piperazinylmethyl]imidazo-[1,2-a]-pyridine
  参考文献：
  名称：

  Searching for multi-target antipsychotics: Discovery of orally active heterocyclic N-phenylpiperazine ligands of D2-like and 5-HT1A receptors

  摘要：

  We described herein the design, synthesis, and pharmacological evaluation of N-phenylpiperazine heterocyclic derivatives as multi-target compounds potentially useful for the treatment of schizophrenia. The isosteric replacement of the heterocyclic ring at the biaryl motif generating pyrazole, 1,2,3-triazole, and 2-methylimidazole[1,2-a]pyridine derivatives resulted in 21 analogues with different substitutions at the para-biaryl and para-phenylpiperazine positions. Among the compounds prepared, 4 (LASSBio-579) and 10 (LASSBio-664) exhibited an adequate binding profile and a potential for schizophrenia positive symptoms treatment without cataleptogenic effects. Structural features of this molecular scaffold are discussed regarding binding affinity and selectivity for D-2-like, 5-HT1A, and 5-HT2A receptors. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.01.040

文献信息

• Searching for multi-target antipsychotics: Discovery of orally active heterocyclic N-phenylpiperazine ligands of D2-like and 5-HT1A receptors
  作者：Gilda Neves、Ricardo Menegatti、Camila B. Antonio、Luiza R. Grazziottin、Renan O. Vieira、Stela M.K. Rates、François Noël、Eliezer J. Barreiro、Carlos A.M. Fraga

  DOI：10.1016/j.bmc.2010.01.040

  日期：2010.3

  We described herein the design, synthesis, and pharmacological evaluation of N-phenylpiperazine heterocyclic derivatives as multi-target compounds potentially useful for the treatment of schizophrenia. The isosteric replacement of the heterocyclic ring at the biaryl motif generating pyrazole, 1,2,3-triazole, and 2-methylimidazole[1,2-a]pyridine derivatives resulted in 21 analogues with different substitutions at the para-biaryl and para-phenylpiperazine positions. Among the compounds prepared, 4 (LASSBio-579) and 10 (LASSBio-664) exhibited an adequate binding profile and a potential for schizophrenia positive symptoms treatment without cataleptogenic effects. Structural features of this molecular scaffold are discussed regarding binding affinity and selectivity for D-2-like, 5-HT1A, and 5-HT2A receptors. (C) 2010 Elsevier Ltd. All rights reserved.