5-Pentyl-5-phenyl-imidazolidine-2,4-dione | 158119-60-9

• 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: 5-Pentyl-5-phenyl-imidazolidine-2,4-dione
• 英文别名: 5-Pentyl-5-phenylhydantoin；5-pentyl-5-phenylimidazolidine-2,4-dione
• CAS: 158119-60-9
• 化学式: C₁₄H₁₈N₂O₂
• 分子量: 246.309
• InChiKey: QAGRPVFBAXEFAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  5-Pentyl-5-phenyl-imidazolidine-2,4-dione 在 盐酸 、 氢氧化钾 、 sodium hydroxide 作用下， 以 丙酮 为溶剂， 反应 28.5h， 生成 2-Amino-2-phenyl-heptanoic acid
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationship Studies for Hydantoins and Analogues as Voltage-Gated Sodium Channel Ligands

  摘要：

  We previously developed a preliminary 3-D QSAR model for the binding of 14 hydantoins to the neuronal voltage-gated sodium channel; this model was successful in designing,an effective non-hydantoin ligand. To further understand structural features that result in optimum binding. here we synthesized a variety of compound classes and evaluated their binding affinities to the neuronal voltage-gated sodium channel using the [H-3]-batrachotoxinin A 20-a-benzoate ([H-3]BTX-B) binding assay. In order to understand the importance of the hydantoin ring for good sodium channel binding, related non-hydantoins such as hydroxy amides, oxazolidinediones, hydroxy acids, and amino acids were included. Two major conclusions were drawn: (1) The hydantoin ring is not critical for compounds with long alkyl side chains, but it is important for compounds with shorter side chains. (2) Relative to Khodorov's pharmacophore. which contains two hydrophobic regions, a third hydrophobic region may enhance binding to provide nanomolar inhibitors.

  DOI：

  10.1021/jm040077o
• 作为产物：
  描述：

  氰化钾 、 苯己酮 、 碳酸氢铵 在 水 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以91%的产率得到5-Pentyl-5-phenyl-imidazolidine-2,4-dione
  参考文献：
  名称：

  log P和苯环构象对5-苯基乙内酰脲与电压依赖性钠通道结合的影响。

  摘要：

  评估了与神经元电压依赖性钠通道（NVSC）的结合，以检测12种5-苯基乙内酰脲，它们系统地改变了log P和/或5-苯基环的取向。log P与乙内酰脲1-12和二苯乙内酰脲（DPH）的体外钠通道结合活性（log IC50）的线性相关性（r2 = 0.638）表明简单分配到脂质相很重要，但不足以说明影响NVSC上的乙内酰脲的含量。比较具有相同log P但低能苯环取向不同的乙内酰脲，发现除log P外，正确的5-苯基取向对于有效结合也很重要。

  DOI：

  10.1021/jm960692v

文献信息

• Effects of log <i>P</i> and Phenyl Ring Conformation on the Binding of 5-Phenylhydantoins to the Voltage-Dependent Sodium Channel
  作者：Milton L. Brown、George B. Brown、Wayne J. Brouillette

  DOI：10.1021/jm960692v

  日期：1997.2.1

  Binding to the neuronal voltage-dependent sodium channel (NVSC) was evaluated for 12 5-phenylhydantoins which systematically varied either log P and/or 5-phenyl ring orientation. The linear correlation of log P with in vitro sodium channel binding activity (log IC50) for hydantoins 1-12 and diphenylhydantoin (DPH) (r2 = 0.638) suggested that simple partitioning into the lipid phase is important but

  评估了与神经元电压依赖性钠通道（NVSC）的结合，以检测12种5-苯基乙内酰脲，它们系统地改变了log P和/或5-苯基环的取向。log P与乙内酰脲1-12和二苯乙内酰脲（DPH）的体外钠通道结合活性（log IC50）的线性相关性（r2 = 0.638）表明简单分配到脂质相很重要，但不足以说明影响NVSC上的乙内酰脲的含量。比较具有相同log P但低能苯环取向不同的乙内酰脲，发现除log P外，正确的5-苯基取向对于有效结合也很重要。
• Modified Bucherer-Bergs Reaction for the One-Pot Synthesis of 5,5′-Disubstituted Hydantoins from Nitriles and Organometallic Reagents
  作者：Michael Shipman、Cyril Montagne

  DOI：10.1055/s-2006-949644

  日期：2006.9

  Diverse sets of 5,5'-disubstituted hydantoins can conveniently be made in moderate to good yields (40-92%) by a one-pot process involving treatment of aromatic, heteroaromatic or aliphatic nitriles with an organometallic reagent (RLi or RMgX) followed by KCN/(NH4)(2)CO3.

  通过一锅法，包括用有机金属试剂（RLi 或 RMgX）处理芳香族、杂芳香族或脂肪族腈，然后以中等至良好的产率 (40-92%) 方便地制备不同组的 5,5'-二取代乙内酰脲通过 KCN/(NH4)(2)CO3。
• Novel therapeutic agents for membrane transporters
  申请人：——

  公开号：US20030044845A1

  公开（公告）日：2003-03-06

  Novel multi-binding compounds (agents) are disclosed which bind cell membrane transporters including ion channels, molecular transporters and ion pumps. The compounds of this invention comprise from 2 to 10 ligands each of which can bind to such cellular transporters to modulate the biological processes/functions thereof. Each of the ligands is covalently attached to a linker (framework) to provide for a multi-binding compound. The linker is selected such that the multi-binding compound exhibits increased modulation of the biological processes/functions of the transporter as compared to the aggregate of the individual ligand units made available for binding to the transporter.

  本发明揭示了一种新型多重结合化合物（试剂），其结合细胞膜转运体，包括离子通道、分子转运体和离子泵。本发明的化合物包括2到10个配体，每个配体都可以结合到这些细胞转运体上，以调节其生物过程/功能。每个配体都共价地连接到一个连接器（框架）上，以提供多重结合化合物。所选择的连接器是为了使多重结合化合物相比可用于结合转运体的单个配体单元的聚合体表现出增强的调节转运体的生物过程/功能的特性。
• EP1089749A4
  申请人：——

  公开号：EP1089749A4

  公开（公告）日：2001-04-11
• NOVEL THERAPEUTIC AGENTS FOR MEMBRANE TRANSPORTERS
  申请人：Advanced Medicine, Inc.

  公开号：EP1089749A1

  公开（公告）日：2001-04-11