2,4-Imidazolidinedione, 5-ethyl-3-(methylsulfonyl)-5-phenyl- | 824392-38-3

• 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: 2,4-Imidazolidinedione, 5-ethyl-3-(methylsulfonyl)-5-phenyl-
• 英文别名: 5-ethyl-3-methylsulfonyl-5-phenylimidazolidine-2,4-dione
• CAS: 824392-38-3
• 化学式: C₁₂H₁₄N₂O₄S
• 分子量: 282.32
• InChiKey: KRNWQOXRNZOOKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  91.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,4-Imidazolidinedione, 5-ethyl-3-(methylsulfonyl)-5-phenyl- 在 盐酸 、 sodium hydroxide 作用下， 以 丙酮 为溶剂， 反应 26.0h， 生成 2-氨基-2-苯丁酸盐酸盐
  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：

  甲基磺酰氯 、 5-乙基-5-苯基海因 在 氢氧化钾 作用下， 以 丙酮 为溶剂， 反应 2.5h， 以62%的产率得到2,4-Imidazolidinedione, 5-ethyl-3-(methylsulfonyl)-5-phenyl-
  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

文献信息

• Synthesis and Structure−Activity Relationship Studies for Hydantoins and Analogues as Voltage-Gated Sodium Channel Ligands
  作者：Congxiang Zha、George B. Brown、Wayne J. Brouillette

  DOI：10.1021/jm040077o

  日期：2004.12.1

  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.