1-(1-苯基乙基)咪唑烷-2,4-二酮 | 86095-58-1

• 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: 1-(1-苯基乙基)咪唑烷-2,4-二酮
• 英文名称: 1-<(R,S)-α-phenylethyl>-hydantoin
• 英文别名: alpha-methylbenzylhydantoin；1-(1-Phenylethyl)imidazolidine-2,4-dione
• CAS: 86095-58-1
• 化学式: C₁₁H₁₂N₂O₂
• 分子量: 204.228
• InChiKey: PUSOBDLIHWGBNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  吗啡啉盐酸盐 、 1-(1-苯基乙基)咪唑烷-2,4-二酮 以71%的产率得到1-(1-phenylethyl)-4-morpholin-4-yl-1,5-dihydroimidazol-2-one
  参考文献：
  名称：

  Synthesis, Pharmacology, and Structure−Activity Relationships of Novel Imidazolones and Pyrrolones as Modulators of GABA_A Receptors

  摘要：

  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.

  DOI：

  10.1021/jm0509400
• 作为产物：
  描述：

  N-<(R)-α-phenylethyl>-hydantoic acid 、 盐酸 以7%的产率得到
  参考文献：
  名称：

  MOSTOWICZ, D.;ABRAMSKI, W.;BELZECKI, C., POL. J. CHEM., 1981, 55, N 6, 1387-1391

  摘要：

  DOI：

文献信息

• Mostowicz, Danuta; Abramski, Wojciech; Belzecki, Czeslaw, Polish Journal of Chemistry, 1981, vol. 55, # 6, p. 1387 - 1391
  作者：Mostowicz, Danuta、Abramski, Wojciech、Belzecki, Czeslaw

  DOI：——

  日期：——
• Process for the preparation of chiral hydantoins, and a novel hydantoin produced by said process and a pharmaceutical composition containing it
  申请人：PFIZER INC.

  公开号：EP0037672B1

  公开（公告）日：1986-05-14
• JPH06343483A
  申请人：——

  公开号：JPH06343483A

  公开（公告）日：1994-12-20
• US4286098A
  申请人：——

  公开号：US4286098A

  公开（公告）日：1981-08-25
• US4348526A
  申请人：——

  公开号：US4348526A

  公开（公告）日：1982-09-07