1-[(2-氯苯基)甲基]咪唑烷-2,4-二酮 | 187243-31-8

• 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-[(2-氯苯基)甲基]咪唑烷-2,4-二酮
• 英文名称: 1-(2-chlorobenzyl)imidazoline-2,4-dione
• 英文别名: 1-[(2-Chlorophenyl)methyl]imidazolidine-2,4-dione
• CAS: 187243-31-8
• 化学式: C₁₀H₉ClN₂O₂
• 分子量: 224.647
• InChiKey: TUVQTCIDQXNTQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 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：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[(2-氯苯基)甲基]咪唑烷-2,4-二酮 、 吗啡啉盐酸盐 以57%的产率得到3-[(2-chlorophenyl)methyl]-5-morpholin-4-yl-4H-imidazol-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

文献信息

• [DE] NEUE, ANTIKONVULSIV WIRKENDE IMIDAZOLIN-2,4-DIONE, DIE IN 1-STELLUNG EINEN ORTHOSUBSTITUIERTEN AR(ALK)YL-REST ENTHALTEN, UND VERFAHREN ZU DEREN HERSTELLUNG<br/>[EN] NOVEL IMIDAZOLINE-2,4-DIONES WITH AN ORTHO-SUBSTITUTED AR(ALK)YL RADICAL IN POSITION 1, HAVING AN ANTI-CONVULSIVE EFFECT, AND PROCESS FOR THEIR PRODUCTION<br/>[FR] NOUVELLES IMIDAZOLIN-2,4-DIONES A EFFET ANTICONVULSIF QUI CONTIENNENT EN POSITION 1 UN RESTE AR(ALK)YLE ORTHOSUBSTITUE ET LEUR PROCEDE DE PREPARATION
  申请人：ARZNEIMITTELWERK DRESDEN GMBH

  公开号：WO1997006149A1

  公开（公告）日：1997-02-20

  (DE) Antikonvulsiv wirkende Verbindungen der allgemeinen Formel (1), worin X = C1-C4-Alkyl, Trifluormethyl, Halogen und Y = Wasserstoff, Halogen bedeuten.(EN) Anti-convulsive compounds of general formula (1) in which X is C1-C4 alkyl, trifluoromethyl, halogen; and Y = hydrogen, halogen.(FR) L'invention concerne des composés à effet anticonvulsif de formule générale (1) dans laquelle X désigne alkyle C1-C4, trifluorométhyle, halogène; et Y désigne hydrogène, halogène.

  （德文）具有抗癫痫作用的化合物，通用配方（1），其中X代表C1-C4烷基、三氟甲基或卤素，Y代表氢或卤素。 （英文）抗癫痫化合物的通用配方（1），其中X为C1-C4烷基、三氟甲基或卤素；Y为氢或卤素。 （法文）本发明涉及具有抗癫痫作用的通用配方（1）化合物，其中X代表C1-C4烷基、三氟甲基或卤素；Y代表氢或卤素。
• NEUE, ANTIKONVULSIV WIRKENDE IMIDAZOLIN-2,4-DIONE, DIE IN 1-STELLUNG EINEN ORTHOSUBSTITUIERTEN AR(ALK)YL-REST ENTHALTEN, UND VERFAHREN ZU DEREN HERSTELLUNG
  申请人：Arzneimittelwerk Dresden GmbH

  公开号：EP0850226A1

  公开（公告）日：1998-07-01
• US5817685A
  申请人：——

  公开号：US5817685A

  公开（公告）日：1998-10-06