3-(4-chlorobutyl)-β-tetralonohydantoin | 206280-23-1

• 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: 3-(4-chlorobutyl)-β-tetralonohydantoin
• 英文别名: 1-(4-chlorobutyl)-3',4'-dihydro-1'H,2H,5H-spiro[imidazolidine-4,2'-naphthalene]-2,5-dione；3'-(4-chlorobutyl)spiro[2,4-dihydro-1H-naphthalene-3,5'-imidazolidine]-2',4'-dione
• CAS: 206280-23-1
• 化学式: C₁₆H₁₉ClN₂O₂
• 分子量: 306.792
• InChiKey: FBFKKHCFDOOLSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  N-苯基哌嗪 、 3-(4-chlorobutyl)-β-tetralonohydantoin 以 乙醇 为溶剂， 反应 17.0h， 以50%的产率得到3'-[4-(4-phenylpiperazin-1-yl)butyl]spiro[2,4-dihydro-1H-naphthalene-3,5'-imidazolidine]-2',4'-dione
  参考文献：
  名称：

  Synthesis and 5-HT1A, 5-HT2A receptor activity of new β-tetralonohydantoins

  摘要：

  A series of new 3-[4-(4-arylpiperazinyl)-butyl]-beta-tetralonohydantoins (8a-13a) were synthesized. The compounds exhibited high affinity for 5-HT1A receptors K-i = 6 to 55 nM) combined with moderate-to-high 5-HT2A receptor aftinities (K-t = 45 to 213 nM). The results of in vivo studies indicated that of the compounds tested, 3-[4-(4-phenylpiperazinyl)-butyl-beta-tetralonohydantoin (8a) showed features of full (pre- and postsynaptic) 5-HT1A receptor agonists, whereas compounds 9a-13a behaved like antagonists of postsynaptic 5-HT1A receptors, additionally, compound 13a produced an effect characteristic of presynaptic 5-HT1A receptor agonists, Moreover, compounds 8aand 10a-13a exhibited properties of 5-HT2A receptor antagonists. Due to the most interesting 5-HT1A/5-HT2A functional profile compounds 8a and 13a were further tested for their potential psychotropic activity. In fact. compound 8a (but not 13a) showed diazepam-like anxiolytic activity and behaved Re a weak antidepressant. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.07.013
• 作为产物：
  描述：

  1-溴-4-氯丁烷 、 替群妥英 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 8.0h， 以80%的产率得到3-(4-chlorobutyl)-β-tetralonohydantoin
  参考文献：
  名称：

  Synthesis and 5-HT1A, 5-HT2A receptor activity of new β-tetralonohydantoins

  摘要：

  A series of new 3-[4-(4-arylpiperazinyl)-butyl]-beta-tetralonohydantoins (8a-13a) were synthesized. The compounds exhibited high affinity for 5-HT1A receptors K-i = 6 to 55 nM) combined with moderate-to-high 5-HT2A receptor aftinities (K-t = 45 to 213 nM). The results of in vivo studies indicated that of the compounds tested, 3-[4-(4-phenylpiperazinyl)-butyl-beta-tetralonohydantoin (8a) showed features of full (pre- and postsynaptic) 5-HT1A receptor agonists, whereas compounds 9a-13a behaved like antagonists of postsynaptic 5-HT1A receptors, additionally, compound 13a produced an effect characteristic of presynaptic 5-HT1A receptor agonists, Moreover, compounds 8aand 10a-13a exhibited properties of 5-HT2A receptor antagonists. Due to the most interesting 5-HT1A/5-HT2A functional profile compounds 8a and 13a were further tested for their potential psychotropic activity. In fact. compound 8a (but not 13a) showed diazepam-like anxiolytic activity and behaved Re a weak antidepressant. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.07.013

文献信息

• Synthesis of N-(4-aryl-1-piperazinylbutyl)-substituted 7,8-benzo-1,3-diazaspiro[4,5]decane-2,4-dione derivatives with potential anxiolytic activity
  作者：Jerzy Kossakowski、Teodor Zawadowski、Jadwiga Turło、Jerzy Kleps

  DOI：10.1016/s0014-827x(98)00010-x

  日期：1998.2

  Continuing our studies connected with the design of new anxiolytics we have now synthesized a series of new compounds, derivatives of 7,8-benzo-1,3-diazaspiro[4,5]decane-2,4-dione bearing a 4-aryl-1-piperazinylbutyl group attached to the imide nitrogen. One single compound was submitted to the 5-HT1A receptor binding assay and found to display the expected-though rather weak-receptorial affinity. (C) 1998 Elsevier Science S.A. All rights reserved.