6-phenyl-1,3-diazaspiro[4.5]decan-2,4-dione | 5007-36-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 6-phenyl-1,3-diazaspiro[4.5]decan-2,4-dione
• 英文别名: 6-phenyl-1,3-diazaspiro[4.5]decane-2,4-dione；6-Phenyl-1.3-diazaspiro<4.5>decan-2.4-dion；6-Phenyl-1,3-diaza-spiro[4.5]decan-2,4-dion
• CAS: 5007-36-3
• 化学式: C₁₄H₁₆N₂O₂
• mdl: MFCD28163817
• 分子量: 244.293
• InChiKey: NKQIMNWNNVAMAV-UHFFFAOYSA-N

物化性质

• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-phenyl-1,3-diazaspiro[4.5]decan-2,4-dione 在 potassium carbonate 、 potassium iodide 作用下， 以 乙二醇甲醚 、 丙酮 为溶剂， 生成 3-{4-[4-(3-chlorophenyl)piperazin-1-yl]butyl}-6-phenyl-1,3-diazaspiro[4,5]decan-2,4-dione
  参考文献：
  名称：

  Novel spirohydantoin derivative as a potent multireceptor-active antipsychotic and antidepressant agent

  摘要：

  A series of novel spirohydantoin derivatives with arylpiperazinylbutyl moiety were synthesized and evaluated for serotonin 5-HT1A, 5-HT2A, 5-HT7 and dopamine D-2 receptors. Based on these data, four compounds were selected for further binding affinity assays on dopamine D-1, D-3, D-4, and 5-HT2C, 5-HT6 as well as adrenergic alpha 1 and alpha(2C) receptors, which are involved in various CNS diseases such as schizophrenia, anxiety and/or depression. The compound 14, 1-{4-[4-(2-metoxyphe-nyl) piperazin-1-yl] butyl}-3',4'-dihydro-2H, 2'H, 5H-spiro[imidazolidine-4,1'-naphthalene]-2,5-dione, with the most promising functional profile, mixed 5-HT2A/D-2 antagonist and 5-HT1A partial agonist, was selected. In the mouse D-amphetamine-induced locomotor hyperactivity model, compound 14 produced antipsychotic-like activity, which is devoid of cataleptogenic effects and in the forced swim test in mice, it showed a significant antidepressant-like effect unlike the reference drug aripiprazole. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.04.026
• 作为产物：
  描述：

  2-苯基环己酮 、 氰化钾 、 alkaline earth salt of/the/ methylsulfuric acid 在 乙醇 作用下， 生成 6-phenyl-1,3-diazaspiro[4.5]decan-2,4-dione
  参考文献：
  名称：

  Tiffeneau; Tchoubar; Saiaslambert, Bulletin de la Societe Chimique de France, 1947, p. 445,448

  摘要：

  DOI：

文献信息

• Novel Lipophilic Hydroxamates Based on Spirocarbocyclic Hydantoin Scaffolds with Potent Antiviral and Trypanocidal Activity
  作者：Vasiliki Pardali、Erofili Giannakopoulou、George Mpekoulis、Vassilina Tsopela、Georgios Panos、Martin C. Taylor、John M. Kelly、Niki Vassilaki、Grigoris Zoidis

  DOI：10.3390/ph16071046

  日期：——

  failures are widely reported. There is an urgent need for new chemotherapies. Based on our previous research, we have undertaken structural modification of lead compound V with the goal of producing derivatives with both antiviral and trypanocidal activity. The novel spirocarbocyclic-substituted hydantoin analogs were designed, synthesized, and tested for antiviral activity against three HCV genotypes

  黄病毒科感染，例如由丙型肝炎 (HCV) 和登革热病毒 (DENV) 引起的感染，代表着全球健康风险。感染者有发展为慢性肝衰竭或出血热的危险，如果不治疗，这两种情况都可能致命。热带寄生虫布氏锥虫和克氏锥虫给撒哈拉以南非洲和拉丁美洲造成了巨大的社会经济负担。抗HCV化疗具有严重的副作用并且价格昂贵，而登革热尚无临床授权的治疗方法。抗寄生虫药物通常有毒且难以施用，并且治疗失败的情况也被广泛报道。迫切需要新的化疗方法。基于我们之前的研究，我们对先导化合物V进行了结构修饰，目的是生产具有抗病毒和杀锥虫活性的衍生物。设计、合成了新型螺碳环取代的乙内酰脲类似物，并测试了其针对三种 HCV 基因型（1b、3a、4a）、DENV、黄热病病毒 (YFV) 和两种锥虫物种（T. brucei、T. cruzi）的抗病毒活性。 ）。优化是成功的，产生的化合物具有显着的抗病毒和杀锥虫活性以及卓越的选择性。为了进一
• Czopek, Anna; Zagórska, Agnieszka; Kołaczkowski, Marcin, Acta poloniae pharmaceutica, 2016, vol. 73, # 6, p. 1545 - 1554
  作者：Czopek, Anna、Zagórska, Agnieszka、Kołaczkowski, Marcin、Bucki, Adam、Gryzło, Beata、Rychtyk, Joanna、Pawłowski, Maciej、Siwek, Agata、Satała, Grzegorz、Bojarski, Andrzej、Kubacka, Monika、Filipek, Barbara

  DOI：——

  日期：——
• Cantarelli,G. et al., Farmaco, Edizione Scientifica, 1975, vol. 30, p. 761 - 772
  作者：Cantarelli,G. et al.

  DOI：——

  日期：——
• Tiffeneau; Tchoubar; Saiaslambert, Bulletin de la Societe Chimique de France, 1947, p. 445,448
  作者：Tiffeneau、Tchoubar、Saiaslambert

  DOI：——

  日期：——
• Novel spirohydantoin derivative as a potent multireceptor-active antipsychotic and antidepressant agent
  作者：Anna Czopek、Marcin Kołaczkowski、Adam Bucki、Hanna Byrtus、Maciej Pawłowski、Grzegorz Kazek、Andrzej J. Bojarski、Agata Piaskowska、Justyna Kalinowska-Tłuścik、Anna Partyka、Anna Wesołowska

  DOI：10.1016/j.bmc.2015.04.026

  日期：2015.7

  A series of novel spirohydantoin derivatives with arylpiperazinylbutyl moiety were synthesized and evaluated for serotonin 5-HT1A, 5-HT2A, 5-HT7 and dopamine D-2 receptors. Based on these data, four compounds were selected for further binding affinity assays on dopamine D-1, D-3, D-4, and 5-HT2C, 5-HT6 as well as adrenergic alpha 1 and alpha(2C) receptors, which are involved in various CNS diseases such as schizophrenia, anxiety and/or depression. The compound 14, 1-4-[4-(2-metoxyphe-nyl) piperazin-1-yl] butyl}-3',4'-dihydro-2H, 2'H, 5H-spiro[imidazolidine-4,1'-naphthalene]-2,5-dione, with the most promising functional profile, mixed 5-HT2A/D-2 antagonist and 5-HT1A partial agonist, was selected. In the mouse D-amphetamine-induced locomotor hyperactivity model, compound 14 produced antipsychotic-like activity, which is devoid of cataleptogenic effects and in the forced swim test in mice, it showed a significant antidepressant-like effect unlike the reference drug aripiprazole. (C) 2015 Elsevier Ltd. All rights reserved.