2-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-1-one | 1443247-69-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-1-one
• 英文别名: 2-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3H-pyrrolo[3,4-b]quinolin-1-one
• CAS: 1443247-69-5
• 化学式: C₂₅H₂₈N₄O₂
• 分子量: 416.523
• InChiKey: GGJPZZMSGBYDMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  48.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  、 1-(3-氨基)-4-(2-甲氧基苯基)哌嗪 以 乙醇 为溶剂， 反应 9.0h， 以78%的产率得到2-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-1-one
  参考文献：
  名称：

  Synthesis and structure–activity relationship studies in serotonin 5-HT1A receptor agonists based on fused pyrrolidone scaffolds

  摘要：

  A new class of serotonin 5-HT1A receptor ligands related to NAN-190, buspirone and aripiprazole has been designed using our potent 5-HT3 receptor ligands as templates. The designed pyrrolidone derivatives 10a-n were prepared by means of the straightforward chemistry consisting in the reaction of the appropriate gamma-haloester derivatives with the suitable mylpiperazinylalkylamines. The nanomolar 5-HT1A receptor affinity and the agonist-like profile shown by fused pyrrolidone derivatives 10k,m stimulated the rationalization of the interaction with an homology model of the 5-HT1A receptor and the evaluation of their selectivity profiles and the pharmacokinetic properties. Interestingly, the results of the profiling assays suggested for close congeners 10k,m a significantly divergent binding pattern with compound 10m showing an appreciable selectivity for 5-HT1AR. (c) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.044

文献信息

• Synthesis and structure–activity relationship studies in serotonin 5-HT1A receptor agonists based on fused pyrrolidone scaffolds
  作者：Andrea Cappelli、Monica Manini、Salvatore Valenti、Federica Castriconi、Germano Giuliani、Maurizio Anzini、Simone Brogi、Stefania Butini、Sandra Gemma、Giuseppe Campiani、Gianluca Giorgi、Laura Mennuni、Marco Lanza、Antonio Giordani、Gianfranco Caselli、Ornella Letari、Francesco Makovec

  DOI：10.1016/j.ejmech.2013.01.044

  日期：2013.5

  A new class of serotonin 5-HT1A receptor ligands related to NAN-190, buspirone and aripiprazole has been designed using our potent 5-HT3 receptor ligands as templates. The designed pyrrolidone derivatives 10a-n were prepared by means of the straightforward chemistry consisting in the reaction of the appropriate gamma-haloester derivatives with the suitable mylpiperazinylalkylamines. The nanomolar 5-HT1A receptor affinity and the agonist-like profile shown by fused pyrrolidone derivatives 10k,m stimulated the rationalization of the interaction with an homology model of the 5-HT1A receptor and the evaluation of their selectivity profiles and the pharmacokinetic properties. Interestingly, the results of the profiling assays suggested for close congeners 10k,m a significantly divergent binding pattern with compound 10m showing an appreciable selectivity for 5-HT1AR. (c) 2013 Elsevier Masson SAS. All rights reserved.