1-p-Anisylhydantoine | 41526-30-1

• 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: 1-p-Anisylhydantoine
• 英文别名: 1-(p-Methoxy-phenyl)-hydantoin；1-(4-methoxyphenyl)hydantoin；1-(4-methoxy-phenyl)-imidazolidine-2,4-dione；1-(4-Methoxy-phenyl)-imidazolidin-2,4-dion；1-(4-methoxyphenyl)imidazolidine-2,4-dione
• CAS: 41526-30-1
• 化学式: C₁₀H₁₀N₂O₃
• mdl: MFCD00225735
• 分子量: 206.201
• InChiKey: WZYTXYBGGKOKTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-p-Anisylhydantoine 在 氢氧化钾 作用下， 反应 24.0h， 以73%的产率得到[1-(4-methoxyphenyl)ureido]acetic acid
  参考文献：
  名称：

  σI Values for Arylureido Groups

  摘要：

  通过对相应的1-芳基咪唑啉-2,4-二酮进行控制碱水解，制备了三种（1-芳基脲基）乙酸。它们及（3-苯基脲基）乙酸的pKa值在25.0°C的0.01 M溶液中通过滴定电位法测定。从酸度常数计算出了四个新的σI常数。

  DOI：

  10.1135/cccc20042276
• 作为产物：
  描述：

  methyl N-cyano-N-(4-methoxyphenyl)glycinate 在 磷酸二丁酯 作用下， 反应 2.0h， 以82%的产率得到1-p-Anisylhydantoine
  参考文献：
  名称：

  在无溶剂条件下高效磷酸二烷基酯介导的乙内酰脲和双环乙内酰脲的合成

  摘要：

  已经通过新策略从基于氰酰胺的前体，即N-氰基-N-烷基/芳基氨基乙酸甲酯合成了不同取代的乙内酰脲。磷酸二烷基酯用作温和的试剂，可在一个步骤中水解和环化底物，以定量获得所需产物。多价乙内酰脲即双乙内酰脲，双环乙内酰脲的合成潜在地扩大了本方法的范围和适用性。无溶剂条件和非常简单的后处理程序使反应变得方便且环保。还报道了一些代表性化合物的单晶结构。

  DOI：

  10.1016/j.tetlet.2011.09.029

文献信息

• Polyfunctional imidazoles: II. Synthesis and reactions with nucleophilic reagents of 1-substituted 2,4-dichloro-1H-imidazole-5-carbaldehydes
  作者：V. A. Chornous、A. M. Grozav、E. B. Rusanov、A. M. Nesterenko、M. V. Vovk

  DOI：10.1134/s1070428011050083

  日期：2011.5

  1-Alkyl(aryl)imidazolidine-2,4-diones reacted with Vilsmeier-Haack reagent affording 1-alkyl(aryl)-2,4-dichloro-1H-imidazole-5-carbaldehydes whose reactions with sodium azide, sodium alkoholates, with phenols, thiols, and secondary cycloalkylamines led to the substitution of chlorine in the position 2 of the imidazole ring. The reaction with primary amines resulted in the condensation products at the

  1-烷基（芳基）咪唑烷-2,4-二酮与Vilsmeier-Haack试剂反应，得到1-烷基（芳基）-2,4-二氯-1 H-咪唑-5-甲醛与叠氮化钠，醇钠，与苯酚，硫醇和仲环烷基胺的反应导致咪唑环2位上的氯取代。与伯胺的反应产生醛基上的缩合产物。
• Aryloxypropanolamine derivatives, pharmaceutical compositions and
  申请人：Pierrel S.p.A.

  公开号：US04579861A1

  公开（公告）日：1986-04-01

  Compounds having general formula I ##STR1## wherein R.sub.1 is hydrogen, lower alkyl, lower alkoxy, alkyl enoxy, halogen, cyano, carboxyamido or ureido group optionally separated from the phenyl ring by a methylene or ethylene bridge; R.sub.2 is hydrogen, halogen, lower alkyl or alkoxy; R.sub.3 is hydrogen, halogen, lower alkyl, lower alkoxy or R.sub.2 and R.sub.3, taken together, are a methylendioxy group; R.sub.4 is hydrogen or lower alkyl, endowed with remarkable cardioselective .beta.-adrenolytic properties, are described. The process for their preparation and pharmaceutical compositions containing them are also described.

  通式I ##STR1## 中的化合物，其中R.sub.1是氢、低烷基、低烷氧基、烷氧基、卤素、氰基、羧胺基或尿素基，可选地与苯环通过亚甲基或乙烯桥分隔；R.sub.2是氢、卤素、低烷基或烷氧基；R.sub.3是氢、卤素、低烷基、低烷氧基或R.sub.2和R.sub.3一起是亚甲二氧基基团；R.sub.4是氢或低烷基，具有显著的心脏选择性β-肾上腺素受体阻滞作用。还描述了它们的制备方法和含有它们的药物组合物。
• Biltz; Slotta, Journal fur praktische Chemie (Leipzig 1954), 1926, vol. <2>113, p. 263 Anm.4
  作者：Biltz、Slotta

  DOI：——

  日期：——
• Pyrrolopyrimidine-inhibitors with hydantoin moiety as spacer can explore P4/S4 interaction on plasmin
  作者：Naoki Teno、Keigo Gohda、Keiko Wanaka、Yuko Tsuda、Takuya Sueda、Yukiko Yamashita、Tadamune Otsubo

  DOI：10.1016/j.bmc.2014.02.002

  日期：2014.4

  In the development of plasmin inhibitors, a novel chemotype, pyrrolopyrimidine scaffold possessing two motifs, a hydantoin-containing P4 moiety and a warhead-containing P1 moiety, is uncovered. A unique feature of the new line of the plasmin inhibitors is that the interaction between the plasmin inhibitors and key subsites in plasmin can be controlled by a spacer like hydantoin. The application of the novel chemotype is demonstrated by 1n and provides further evidence on the importance of hydantoin as the spacer. (c) 2014 Elsevier Ltd. All rights reserved.
• Synthesis, Pharmacology, and Structure−Activity Relationships of Novel Imidazolones and Pyrrolones as Modulators of GABA_A Receptors
  作者：Christian Grunwald、Chris Rundfeldt、Hans-Joachim Lankau、Thomas Arnold、Norbert Höfgen、Rita Dost、Ute Egerland、Hans-Jörg Hofmann、Klaus Unverferth

  DOI：10.1021/jm0509400

  日期：2006.3.1

  New series of imidazolones and pyrrolones were synthesized. The compounds were tested regarding their anxiolytic properties due to modulation of the GABA(A) receptor response. Several derivatives exhibit considerable pharmacological activity while lacking the typical side effects of benzodiazepine receptor agonists. 1-(4-chlorophenyl)-4-morpholin-1-yl-1,5-dihydro-imidazol-2-one (2) and 1-(4-chlorophenyl)-4-piperidin-1-yl-1,5-dihydro-imidazol-2-one (3) were protective in the pentylenetetrazole test in rats with oral ED50 of 27.4 and 12.8 mg/kg and TD50 (rotarod) of > 500 and 265 mg/kg, respectively. The minimum effective dose in the Vogel conflict test was 3 mg/kg for both compounds. Common structure-activity relationship and comparative molecular field analysis models of the various series of derivatives could be established which are in accordance with a GABAA mediated pharmacological action. The findings fit well into an established pharmacophore model. This model is refined by an additional steric restriction feature.