NSC 1023 | 5394-37-6

• 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: NSC 1023
• 英文别名: 5-phenyl-5-propyl-imidazolidine-2,4-dione；5-Phenyl-5-propyl-imidazolidin-2,4-dion；5-Phenyl-5-propylimidazolidine-2,4-dione
• CAS: 5394-37-6
• 化学式: C₁₂H₁₄N₂O₂
• mdl: MFCD00068879
• 分子量: 218.255
• InChiKey: NLEOJRZVVDXEBJ-UHFFFAOYSA-N

物化性质

• 溶解度：
  >32.7 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 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：

  N-[4-(2-bromo-acetyl)-3-fluoro-phenyl]-acetamide 、 NSC 1023 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 0.08h， 以81%的产率得到(+/-)-N-{4-[2-(2,5-dioxo-4-phenyl-4-propyl-imidazolidin-1-yl)-acetyl]-3-fluoro-phenyl}-acetamide
  参考文献：
  名称：

  ORGANIC COMPOUNDS

  摘要：

  本发明涉及式(I)的化合物，其中取代基如规范中所定义；以自由碱或酸盐形式存在；其制备方法，以及其作为药物的用途和包含它的药物。

  公开号：

  US20090099243A1
• 作为产物：
  描述：

  2-Propyl-2-phenyl-cyanacetamid 在 sodium hypobromide 作用下， 生成 NSC 1023
  参考文献：
  名称：

  Thompson; Bedell; Buffett, Journal of the American Chemical Society, 1925, vol. 47, p. 875

  摘要：

  DOI：

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。
• Synthesis, structure, and solvatochromic properties of pharmacologically active 5-substituted 5-phenylhydantoins
  作者：Nemanja Trišović、Nataša Valentić、Marko Erović、Tatjana Đaković-Sekulić、Gordana Ušćumlić、Ivan Juranić

  DOI：10.1007/s00706-011-0639-7

  日期：2011.12

  200–400 nm in selected solvents of different polarity. The effects of solvent dipolarity/polarizability and solvent–solute hydrogen-bonding interactions were analyzed by means of the linear solvation energy relationship concept proposed by Kamlet and Taft. The lipophilicities of the investigated hydantoins were estimated by calculation of their log P values. The quantitative relationship between the ratio

  摘要合成了一系列5-取代的5-苯基乙内酰脲，并在不同极性的选定溶剂中于200-400 nm范围内记录了它们的紫外吸收光谱。借助Kamlet和Taft提出的线性溶剂化能量关系概念，分析了溶剂的偶极/极化性和溶剂-溶质氢键相互作用的影响。通过计算它们的log P值来估计所研究的乙内酰脲的亲脂性 。讨论了特定溶剂相互作用的贡献比与相应的亲脂性参数之间的定量关系。相关方程式与相应的ED 50组合值和不同的理化参数来生成新的方程式，以证明溶质-溶剂相互作用与结构-活性参数之间的合理关系。为了确定不同溶剂中吸收带的光谱分配，进行了量子化学计算。 图形概要
• [EN] 5-[3-[PIPERIDIN-1-YL]-3-OXO-PROPYL]-IMIDAZOLIDINE-2,4-DIONE DERIVATIVES AS ADAMTS 4 AND 5 INHIBITORS FOR TREATING E.G. OSTEOARTHRITIS<br/>[FR] DÉRIVÉS DE 5-[3-[PIPÉRIDIN-1-YL]-3-OXO-PROPYL]-IMIDAZOLIDINE-2,4-DIONE EN TANT QU'INHIBITEURS D'ADAMTS 4 ET 5 POUR LE TRAITEMENT, PAR EXEMPLE, DE L'ARTHROSE
  申请人：GALAPAGOS NV

  公开号：WO2017211667A1

  公开（公告）日：2017-12-14

  The present invention discloses 5-[3-[piperazin-l-yl]-3-oxo-propyl]-imidazolidine-2,4-dione derivatives according to Formula (I), wherein R1, R2, R3a, R3b, R6a, R6b, the subscript n and Cy are as defined herein. The present invention relates to compounds inhibiting ADAMTS 4 and 5 for the prophylaxis or treatment of inflammatory diseases or diseases involving degradation of cartilage or disruption of cartilage homeostasis, such as e.g. osteoarthritis.

  本发明揭示了根据式(I)的5-[3-[哌嗪-1-基]-3-氧代丙基]-咪唑啉-2,4-二酮衍生物，其中R1、R2、R3a、R3b、R6a、R6b、下标n和Cy如本文所定义。本发明涉及抑制ADAMTS 4和5的化合物，用于预防或治疗炎症性疾病或涉及软骨降解或软骨稳态破坏的疾病，例如骨关节炎。
• 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.
• Novelli, Anales des la Asociacion Quimica Argentina, 1941, vol. 29, p. 83,85
  作者：Novelli

  DOI：——

  日期：——