5,5-二苄基咪唑烷-2,4-二酮 | 23186-94-9

• 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: 5,5-二苄基咪唑烷-2,4-二酮
• 英文名称: 5,5-di-benzyl-hydantoin
• 英文别名: 5,5-dibenzyhydantoin；5,5-dibenzyl-imidazolidine-2,4-dione；5,5-Dibenzyl-imidazolidin-2,4-dion；5,5-dibenzylhydantoin；4.4-Dibenzyl-2.5-dioxo-imidazolidin；5,5-Dibenzyl-hydantoin；5,5-Dibenzylimidazolidine-2,4-dione
• CAS: 23186-94-9
• 化学式: C₁₇H₁₆N₂O₂
• mdl: MFCD00841868
• 分子量: 280.326
• InChiKey: RKEFYRGLENJHMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 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：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  5,5-二苄基咪唑烷-2,4-二酮 在 barium dihydroxide 作用下， 生成 2-氨基-2-苄基-3-苯基丙酸
  参考文献：
  名称：

  Potential Growth Antagonists. I. Hydantoins and Disubstituted Glycines^1,2

  摘要：

  DOI：

  10.1021/jo01081a024
• 作为产物：
  描述：

  2-Aminocarbonyl-2-cyano-1,3-diphenylpropane 在 氢氧化钾 、 溴 作用下， 生成 5,5-二苄基咪唑烷-2,4-二酮
  参考文献：
  名称：

  Errera, Gazzetta Chimica Italiana, 1896, vol. 26 I, p. 201

  摘要：

  DOI：

文献信息

• Phenceptin: a biomimetic model of the phenytoin receptor
  作者：Saul Wolfe、Raymond John Bowers、Hee-Sook Shin、Chang-Kook Sohn、Donald Fredric Weaver、Kiyull Yang

  DOI：10.1139/v88-425

  日期：1988.11.1

  5,5-Diphenylhydanytoin (phenytoin) is the most widely used anticonvulsant drug, but has many side effects. Although its chemical mode of action is unknown, phenytoin is believed to function primarily by interference with the transport of sodium ions across the neuronal membrane. Structure–activity and lipophilicity–activity studies suggest that the drug interacts with its receptor through hydrogen bonding to the N3—C4 amide bond, and an aromatic–aromatic interaction with the C5 substituent. Since sodium channels are cysteine-rich peptides, whose function depends upon the cysteine[Formula: see text]cystine redox process, it has been hypothesized that the action of the phenytoin receptor may be mimicked by a properly designed cyclodepsipeptide containing a cystinyl moiety, a cavity lined with five oxygen atoms oriented in the trigonal-bipyramidal manner appropriate for selective transport of sodium ions, and a site for the binding of phenytoin. A computer programme and strategy were developed to permit the three-dimensional structures of potential target molecules to be viewed, prior to synthesis. Use of this programme led to the discovery of Boc-L-cystinyl-glycyl-L-prolyl-glycyl-L-prolyl-L-cystine-OCHPh₂. This compound, termed phenceptin, was synthesized from a linear precursor containing tert-butoxycarbonyl protection at the N-terminus, benzhydryl ester protection at the C-terminus, and trityl protection at sulfur. Detritylation and cyclization to phenceptin were accomplished with iodine in methanol–pyridine. Using an n-octanol membrane to study the kinetics of ion transport, phenceptin was found to transport sodium ions selectively, but only in its oxidized, cyclic form. This transport was inhibited significantly by one mol-equiv. of phenytoin, and not at all by biologically inactive analogs of the drug. The nature of the binding of phenytoin to phenceptin was examined by nuclear magnetic resonance, in n-C₈D₁₇-OH solvent, and found to involve hydrogen bonding of the drug to a glycine residue whose oxygen atom is involved in complexation to sodium ions.

  5,5-二苯基肼（苯妥英）是最广泛使用的抗癫痫药物，但具有许多副作用。尽管其化学作用方式尚不清楚，但人们认为苯妥英主要通过干扰神经元膜上钠离子的传输来发挥作用。结构活性和亲脂性活性研究表明，该药物通过氢键与N3—C4酰胺键以及与C5取代基的芳香-芳香相互作用与其受体相互作用。由于钠通道是富含半胱氨酸的肽，其功能取决于半胱氨酸[公式：见文本]半胱氨酸氧化还原过程，有人假设苯妥英受体的作用可能被一个设计良好的环脱氨肽所模拟，其中包含一个半胱氨酸基团、一个以三角双锥方式定向排列的五个氧原子构成的腔，适合选择性地传输钠离子，并且有一个结合苯妥英的位点。开发了一个计算程序和策略，允许在合成之前查看潜在靶分子的三维结构。使用该程序导致发现了Boc-L-半胱氨酰基-L-甘氨酰-L-脯氨酰基-L-甘氨酰-L-脯氨酰-L-半胱氨酸-OCHPh₂。这种化合物被称为苯塞普汀，它是从一个线性前体合成的，该前体在N-末端具有叔丁氧羰保护基，在C-末端具有苄基酯保护基，在硫上具有三苄基保护基。用碘在甲醇-吡啶中进行去三苄基化和环化制备苯塞普汀。使用正辛醇膜研究离子传输动力学，发现苯塞普汀只在其氧化的环状形式中选择性地传输钠离子。这种传输受到苯妥英一个当量的显著抑制，而对于该药物的生物非活性类似物则完全没有抑制作用。通过核磁共振在n-C₈D₁₇-OH溶剂中研究苯妥英与苯塞普汀的结合性质，发现药物与一个氧原子参与与钠离子络合的甘氨酸残基之间的氢键结合。
• Anti-fibril peptides
  申请人：Hammer P. Robert

  公开号：US20050119187A1

  公开（公告）日：2005-06-02

  Short peptides containing C α,α -dipropylglycine (Dpg) at alternating sequence positions were synthesized and examined for conformational behavior. Peptide assembly was performed using Fmoc-solid-phase chemistry where the coupling with PyAOP could be significantly enhanced at elevated temperature. Circular dichroism (CD) and NMR conformational studies revealed that incorporation of Dpg residues induced folded structures into peptides. It was observed that Dpg residues adopted helical conformation in a helix-promoting sequence. The resulting helical structure was comprised of consecutive β-turns whose structure was stabilized by salt bridge in aqueous solution. In this study, the preparation of sterically and polyfunctional C α,α -disubstituted amino acids (ααAAs) via alkylation of ethyl nitroacetate and transformation into derivatives ready for incorporation into peptides are described. Treatment of ethyl nitroacetate with N,N-diisopropylethylamine in the presence of a catalytic amount of tetraalkylammonium salt, followed by the addition of an activated alkyl halide or Michael acceptor, gave the doubly C-alkylated product in good to excellent yields. Selective nitro reduction with Zn in acetic or hydrogen over Raney Ni gave the corresponding amino ester that, upon saponification, can be protected with the fluorenylmethyloxycarbonyl (Fmoc) group. The synthesis of a sterically demanding C α,α -dibenzylglycine (Dbzg), and an orthogonally protected, tetrafunctional C α,α -disubstituted analogue of aspartic acid Bcmg is described. The preparation of amyloid fibril blocker peptides based on amyloid peptide hydrophobic core Aβ 16-20 is described. These blocker peptides containing sterically

  含有Cα，α-二丙基甘氨酸（Dpg）的短肽序列被合成并检测其构象行为。肽组装使用Fmoc固相化学方法进行，其中与PyAOP的偶联可以在升高的温度下显著增强。圆二色性（CD）和NMR构象研究表明，Dpg残基的引入使肽中产生了折叠结构。观察到Dpg残基在螺旋促进序列中采用螺旋构象。所得到的螺旋结构由连续的β-转角组成，在水溶液中由盐桥稳定其结构。本研究介绍了通过乙基硝酸酯的烷基化和转化成准备好用于肽中的衍生物来制备立体和多功能的Cα，α-二取代氨基酸（ααAAs）的方法。在四烷基铵盐的催化下，将乙基硝酸酯与N，N-二异丙基乙基胺反应，然后加入活化的烷基卤或迈克尔受体，以良好至优良的收率得到双重C-烷基化产物。在乙酸或Raney Ni的氢中，用Zn选择性还原硝基，得到相应的氨基酸酯，经皂化后可以用芴甲氧羰基（Fmoc）基团保护。介绍了一种立体要求高的Cα，α-二苄基甘氨酸（Dbzg）和一个正交保护的、四功能的Cα，α-二取代天冬氨酸类似物Bcmg的合成方法。介绍了基于淀粉样蛋白肽疏水核心Aβ16-20的淀粉样纤维阻滞肽的制备方法。这些阻滞肽含有立体的残基，可以阻止淀粉样纤维的形成。
• Investigation of tetrasubstituted heterocycles reveals hydantoins as a promising scaffold for development of novel antimicrobials with membranolytic properties
  作者：Manuel K. Langer、Ataur Rahman、Hymonti Dey、Trude Anderssen、Hans-Matti Blencke、Tor Haug、Klara Stensvåg、Morten B. Strøm、Annette Bayer

  DOI：10.1016/j.ejmech.2023.115147

  日期：2023.3

  for drug lead development. Subsequently, a total of 20 hydantoin derivatives were studied for their antimicrobial potency and haemolytic activity. We found 19 of these derivatives to have very low haemolytic toxicity and identified three lead structures, 2dA, 6cG, and 6dG with very promising broad-spectrum antimicrobial activity. Lead structure 6dG displayed minimum inhibitory concentration (MIC) values

  抗菌肽 (AMP) 的模拟物已被提议作为一类有前途的抗菌剂。我们报告了五种四取代、阳离子、两亲性杂环化合物作为潜在 AMP 模拟物的分析。分析表明，杂环支架对化合物的溶血活性有很大影响，乙内酰脲支架被确定为药物先导开发的有前途的模板。随后，研究了总共 20 种乙内酰脲衍生物的抗菌效力和溶血活性。我们发现这些衍生物中的 19 种具有非常低的溶血毒性，并确定了具有非常有前途的广谱抗菌活性的三个先导结构2dA、6cG和6dG 。铅结构6dG对革兰氏阳性菌的最低抑菌浓度 (MIC) 值低至 1 μg/mL，对革兰氏阴性菌的最低抑菌浓度 (MIC) 值低至 4–16 μg/mL。利用基于荧光素酶的生物传感器测定法对胺衍生物6cG进行的初始作用模式 (MoA) 研究表明，它对大肠杆菌的外膜和内膜具有强烈的膜破坏作用。我们的研究结果表明，由杂环支架诱导的物理特性和结构排列是 AMP 模拟物设计的重要因素。
• POLYACETAL RESIN COMPOSITION
  申请人：Polyplastics Co., Ltd.

  公开号：EP1674526A1

  公开（公告）日：2006-06-28

  A polyacetal resin composition comprises a polyacetal resin, and at least one carboxylic acid hydrazide selected from a saturated or unsaturated long-chain aliphatic carboxylic acid hydrazide, a saturated or unsaturated alicyclic carboxylic acid hydrazide, a dimer acid or trimer acid hydrazide, and an oxycarboxylic acid hydrazide corresponding to each of these hydrazides. The proportion of the carboxylic acid hydrazide may be about 0.001 to 20 parts by weight relative to 100 parts by weight of the polyacetal resin. The polyacetal resin composition may further comprise at least one member selected from an antioxidant, a heat stabilizer, a processing stabilizer, a weather (light)-resistant stabilizer, an impact resistance improver, a slip-improving agent, a coloring agent, and a filler. With the use of such a resin composition, stability of a polyacetal resin is improved, and formaldehyde emission is inhibited.

  聚缩醛树脂组合物由聚缩醛树脂和至少一种羧酸酰肼组成，羧酸酰肼选自饱和或不饱和长链脂族羧酸酰肼、饱和或不饱和脂环族羧酸酰肼、二聚酸或三聚酸酰肼以及与上述每种酰肼相对应的氧羧酸酰肼。相对于 100 重量份的聚缩醛树脂，羧酸酰肼的比例可以是约 0.001 至 20 重量份。聚缩醛树脂组合物还可以包含至少一种选自抗氧化剂、热稳定剂、加工稳定剂、耐候（光）稳定剂、抗冲击性改进剂、滑爽性改进剂、着色剂和填料的成分。使用这种树脂组合物可以提高聚缩醛树脂的稳定性，并抑制甲醛释放。
• ALDEHYDE INHIBITOR COMPOSITION AND POLYACETAL RESIN COMPOSITION
  申请人：Polyplastics Co., Ltd.

  公开号：EP1683838A1

  公开（公告）日：2006-07-26

  An aldehyde-inhibiting composition inhibiting an aldehyde from an aldehyde-generating source comprises a carboxylic acid hydrazide and a metal salt of a hydroxy polycarboxylic acid (e.g., a salt of citric acid, malic acid, or tartaric acid with an alkaline earth metal) in a proportion of 0.01 to 100 parts by weight relative to 1 part by weight of the carboxylic acidhydrazide. Moreover, a polyacetal resin composition may comprise a polyacetal resin and the aldehyde-inhibiting composition in a proportion of 0.001 to 20 parts by weight of the aldehyde-inhibiting composition relative to 100 parts by weight of the polyacetal resin. To the resin composition, may be added an antioxidant, a heat stabilizer, a processing stabilizer, a weather (light)-resistant stabilizer, an impact resistance improver, a gloss control agent, a sliding improver, a coloring agent, a filler, and others. A small amount of the aldehyde-inhibiting composition efficiently inhibits the aldehyde generation from the polyacetal resin without discoloring the resin.

  一种抑制醛生成源的醛的抑醛组合物包括羧酸酰肼和羟基多羧酸的金属盐（如柠檬酸、苹果酸或酒石酸与碱土金属的盐），相对于 1 份羧酸酰肼的重量比例为 0.01 至 100 份。此外，聚缩醛树脂组合物可包括聚缩醛树脂和醛抑制组合物，其中醛抑制组合物的比例为 0.001 至 20（按聚缩醛树脂的重量计），相对于 100（按聚缩醛树脂的重量计）。在树脂组合物中可添加抗氧化剂、热稳定剂、加工稳定剂、耐候（光）稳定剂、抗冲击性改进剂、光泽控制剂、滑动改进剂、着色剂、填料等。少量的醛抑制组合物就能有效抑制聚缩醛树脂中醛的生成，而不会使树脂变色。