5,5-双-(4-甲氧基苯基)-咪唑烷-2,4-二酮 | 2402-44-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: 5,5-双-(4-甲氧基苯基)-咪唑烷-2,4-二酮
• 英文名称: 5,5-di-(4-methoxyphenyl)-hydantoin
• 英文别名: 5,5-bis-(4-methoxy-phenyl)-imidazolidine-2,4-dione；5,5-Bis-(4-methoxy-phenyl)-imidazolidin-2,4-dion；5,5-di(4-methoxyphenyl)hydantoin；5,5-Bis-(4-methoxy-phenyl)-hydantoin；5,5-Bis-(p-methoxyphenyl)-hydantoin；5,5-Bis(4-methoxyphenyl)imidazolidine-2,4-dione
• CAS: 2402-44-0
• 化学式: C₁₇H₁₆N₂O₄
• mdl: MFCD03658060
• 分子量: 312.325
• InChiKey: HUULDKVZAIILJR-UHFFFAOYSA-N

物化性质

• 熔点：
  225 °C
• 密度：
  1.256±0.06 g/cm3(Predicted)
• 溶解度：
  >46.8 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.176
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  5,5-双-(4-甲氧基苯基)-咪唑烷-2,4-二酮 在 三苯基膦 、 红铝 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 28.0h， 生成 3-(1-Benzyl-piperidin-4-yl)-5,5-di-(4-methoxyphenyl)-imidazolidin-2-one
  参考文献：
  名称：

  Discovery of Diaryl Imidazolidin-2-one Derivatives, a Novel Class of Muscarinic M3 Selective Antagonists (Part 1)

  摘要：

  Pharmacophore-based structural identification, synthesis, and structure-activity relationships of a new class of muscarinic M3 receptor antagonists, the diaryl imidazolidin-2-one derivatives, are described. The versatility of the discovered scaffold allowed for several structural modifications that resulted in the discovery of two distinct classes of compounds, specifically a class of tertiary amine derivatives (potentially useful for the treatment of overactive bladder by oral administration) and a class of quaternary ammonium salt derivatives (potentially useful for the treatment of respiratory diseases by the inhalation route of administration). In this paper, we describe the synthesis and biological activity of tertiary amine derivatives. For these compounds, selectivity for the M3 receptor toward the M2 receptor was crucial, because the M2 receptor subtype is mainly responsible for adverse systemic side effects of currently marketed muscarinic antagonists. Compound 50 showed the highest selectivity versus M2 receptor, with binding affinity for M3 receptor K-i = 4.8 nM and for M2 receptor K-i = 1141 nM. Functional in vitro studies on selected compounds confirmed the antagonist activity toward the M3 receptor and functional selectivity toward the M2 receptor.

  DOI：

  10.1021/jm061159a
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 alkaline permanganate 作用下， 生成 5,5-双-(4-甲氧基苯基)-咪唑烷-2,4-二酮
  参考文献：
  名称：

  Biltz, Chemische Berichte, 1909, vol. 42, p. 1799

  摘要：

  DOI：

文献信息

• Chitosan decorated Fe₃O₄nanoparticles as a magnetic catalyst in the synthesis of phenytoin derivatives
  作者：Javad Safari、Leila Javadian

  DOI：10.1039/c4ra06618a

  日期：——

  In the present work, Fe3O4 nanoparticles were synthesized by the chemical coprecipitation process. Subsequently, the synthesized nanoparticles were modified with chitosan by a simple method and characterized by X-ray diffractometry (XRD), Fourier transform infrared spectrophotometry (FT-IR), vibrating sample magnetometry (VSM), scanning electron microscopy (SEM) and energy-dispersive X-ray spectroscopy (EDX). Then, phenytoin derivatives were catalyzed by magnetic Fe3O4–chitosan nanoparticles. Fe3O4–chitosan nanoparticles were found to be a recoverable organocatalyst for the efficient synthesis of 5,5-diphenylhydantoins and 5,5-diphenyl-2-thiohydantoins from substituted benzils and urea or thiourea derivatives. The nanocatalyst could be recovered easily under a magnetic field for reuse, and considerable loss of its catalytic activity was not observed after reuse in seven consecutive runs.

  本研究采用化学共沉淀法合成了 Fe3O4 纳米粒子。随后，用简单的方法对合成的纳米粒子进行壳聚糖修饰，并通过 X 射线衍射仪（XRD）、傅立叶变换红外分光光度法（FT-IR）、振动样品磁力计（VSM）、扫描电子显微镜（SEM）和能量色散 X 射线光谱（EDX）对其进行表征。然后，用磁性 Fe3O4 壳聚糖纳米颗粒催化苯妥英衍生物。研究发现，Fe3O4-壳聚糖纳米颗粒是一种可回收的有机催化剂，可从取代的苯并芘和脲或硫脲衍生物中高效合成 5,5-二苯基海因和 5,5-二苯基-2-硫代海因。该纳米催化剂可在磁场下轻松回收再利用，连续七次重复使用后也未发现其催化活性有明显下降。
• Therapeutic method of treating cardiac arrhythmias utilizing
  申请人：Miles Laboratories, Inc.

  公开号：US04006232A1

  公开（公告）日：1977-02-01

  3-substituted-5,5-diphenylhydantoin derivatives in which the 5,5-diphenylhydantoin moiety is attached at C.sub.3 by a loweralkylene bridge to a 4-phenyl-1-piperidyl, 4-hydroxy-4-phenyl-1-piperidyl, 4-phenyl-1,2,3,6-tetrahydropyridyl, 4-phenyl-1-piperazinyl, or loweralkylamino group are useful in the treatment of cardiac arrhythmias in mammals. One or both of the 5,5-diphenyl substituents optionally can be substituted in the ortho-, meta-, or para-positions with halogeno, lowerakyl, loweralkoxy, amino or nitro groups.

  3-取代-5,5-二苯基海达嗪衍生物，其中5,5-二苯基海达嗪基团通过较低的烷基桥连接到C.sub.3处，形成4-苯基-1-哌啶基、4-羟基-4-苯基-1-哌啶基、4-苯基-1,2,3,6-四氢吡啶基、4-苯基-1-哌嗪基或较低的烷基氨基团，在哺乳动物心律失常的治疗中是有用的。其中一个或两个5,5-二苯基取代基可以选择性地在邻位、间位或对位与卤素、较低烷基、较低烷氧基、氨基或硝基团进行取代。
• Synthesis and dynamic NMR studies of novel hydantoin and thiohydantoin derivatives. Crystal structure of diethyl 2-(4,4-diaryl-2,5-dioxoimidazolidin-1-yl) fumarate and diethyl 2-(4,4-diaryl-2-mercapto-5-oxo-4,5-dihydro-1<i>H</i>-imidazol-1-yl)fumarate
  作者：Mohammad M. Ghanbari、Marzieh Jamali、Gyula Batta、Attila C. Bényei

  DOI：10.3184/174751917x14932244903881

  日期：2017.5

  dialkyl 2-(4,4-diaryl-2-mercapto-5-oxo-4,5-dihydro-1H-imidazol-1-yl)fumarate, 7. Single crystal X-ray diffraction study on 4b and 7b proved the structures unambiguously with C=O and SH functionality at the 2-position of the imidazole ring, respectively. Dynamic effects were observed in the NMR spectra of these compounds and were attributed to restricted rotation around the carbon-nitrogen single bonds

  在乙内酰脲或硫代乙内酰脲的存在下，化学计量的二烷基乙炔二羧酸酯与三苯基膦的反应提供了稳定的结晶磷叶立德。这些化合物经历 PPh3 的平滑消除以产生二烷基 2-(4,4-diaryl-2,5-dioxoimidazolidin-1-yl)fumarate、4 或二烷基 2-(4,4-diaryl-2-mercapto-5-oxo -4,5-dihydro-1H-imidazol-1-yl)fumarate, 7. 4b 和 7b 的单晶 X 射线衍射研究清楚地证明了在咪唑环的 2-位具有 C=O 和 SH 官能团的结构， 分别。在这些化合物的 NMR 光谱中观察到动态效应，这归因于围绕碳 - 氮单键的受限旋转。旋转异构体的相互转化过程的旋转能垒 (ΔG#) 等于 (53.6 和 17.2) ± 2 kcal mol-1。
• Topical pharmaceutical composition containing phenytoin and a (co-) analgesic for the treatment of chronic pain
  申请人：Topical Innovations B.V.

  公开号：US11147799B2

  公开（公告）日：2021-10-19

  This disclosure relates to a pharmaceutical composition for topical use wherein the active pharmaceutical ingredient consists of the co-analgesic phenytoin and at least one further co-analgesic, and a method for producing the pharmaceutical composition. In addition, the disclosure relates to the pharmaceutical composition for use in the treatment of chronic pain.

  本公开涉及一种局部使用的药物组合物，其中的活性药物成分包括共镇痛剂苯妥英和至少另一种共镇痛剂，还涉及一种生产该药物组合物的方法。此外，本发明还涉及用于治疗慢性疼痛的药物组合物。
• Topical phenytoin for use in the treatment of peripheral neuropathic pain
  申请人：Topical Innovations B.V.

  公开号：US11285099B2

  公开（公告）日：2022-03-29

  The present disclosure relates to pharmaceutical compositions containing phenytoin or phenytoin sodium for use in topical pain relief. Use of the pharmaceutical composition of the disclosure reduces peripheral neuropathic pain. The topical pharmaceutical compositions of the disclosure containing phenytoin or phenytoin sodium, surprisingly reduce peripheral neuropathic pain considerably, especially and preferably in the conditions, characterized by a low to moderate grade of peripheral neurogenic inflammation, such as small fiber neuropathy, diabetic neuropathy, chronic idiopathic axonal polyneuropathy, post-herpetic neuralgia, trigeminus neuralgia, chemotherapy induced polyneuropathy, traumatic neuropathies, compression neuropathies, and infectious neuropathies in remission, according to the disclosure.

  本公开涉及用于局部止痛的含有苯妥英或苯妥英钠的药物组合物。使用本公开的药物组合物可以减轻外周神经病理性疼痛。含有苯妥英或苯妥英钠的本公开的外用药物组合物能令人惊讶地显著减轻外周神经病理性疼痛，特别是在以中低度外周神经源性炎症为特征的情况下、根据本发明，这些病症包括小纤维神经病变、糖尿病神经病变、慢性特发性轴索性多发性神经病变、带状疱疹后神经痛、三叉神经痛、化疗诱发的多发性神经病变、创伤性神经病变、压迫性神经病变和缓解期感染性神经病变。