3-(2-phenylethylamino)-tetrahydrofuran-2-one | 765256-18-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-(2-phenylethylamino)-tetrahydrofuran-2-one
• 英文别名: 3-(2-Phenylethylamino)oxolan-2-one
• CAS: 765256-18-6
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: GSIZCCMOHVVUPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-二甲氧基苄胺 、 3-(2-phenylethylamino)-tetrahydrofuran-2-one 以 甲苯 为溶剂， 反应 12.0h， 生成 N-[(3,4-dimethoxyphenyl)methyl]-4-hydroxy-2-(2-phenylethylamino)butanamide
  参考文献：
  名称：

  Synthesis, Physicochemical Properties, Anticonvulsant Activities, and GABA-ergic and Voltage-sensitive Calcium Channel Receptor Affinities of α-SubstitutedN-Benzylamides of γ-Hydroxybutyric Acid Part 4: Search for New Anticonvulsant Compounds

  摘要：

  In a search for new anticonvulsant compounds, two series of N-benzylamides of alpha-(benzylamino)-gamma-hydroxybutyric acid (series A) and alpha-(2-phenylethylamino)-gamma-hydroxybutyric acid (series B), were investigated in maximal electroshock (MES), subcutaneous metrazole, and rotorod toxicity assays. The most,potent anticonvulsant compounds were alpha-(benzylamino)-gamma-hydroxybutyric acid N-benzylamide (3) and N-(2-chlorobenzyl-amide (4) with median effective (ED50) doses 63.0 mg/kg and , respectively. alpha-(4-Phenylpiperazinyl-gamma-hydroxy-butyric acid N-(4-methylbenzyl)amide (17) and alpha-(benzylpiperaz-inyl-gamma-hydroxy-butyric acid N-(4-methylbenzyl)amide (18) were also tested for their ability to potentiate [H-3] -muscimol binding and Ifo inhibit [S-35]-TBPS binding (as indices of GABA-A receptor potentiation). Amide 17 exhibited activity at the GABA-A complex which may be the mechanism by which the anticonvulsant effect of this compound is mediated. The N-benzylamides of alpha-(benzylamino)-gamma-hydroxybutyric acid (3-9) were also evaluated for their ability to displace [H-3] nitrendipine from voltage-sensitive calcium channel (VSCC) receptors isolated from rat cortex.

  DOI：

  10.1002/(sici)1521-4184(19995)332:5<167::aid-ardp167>3.0.co;2-n
• 作为产物：
  描述：

  α-溴-γ-丁内酯 、 2-苯乙胺 在 四丁基溴化铵 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 3-(2-phenylethylamino)-tetrahydrofuran-2-one
  参考文献：
  名称：

  Synthesis, Physicochemical Properties, Anticonvulsant Activities, and GABA-ergic and Voltage-sensitive Calcium Channel Receptor Affinities of α-SubstitutedN-Benzylamides of γ-Hydroxybutyric Acid Part 4: Search for New Anticonvulsant Compounds

  摘要：

  In a search for new anticonvulsant compounds, two series of N-benzylamides of alpha-(benzylamino)-gamma-hydroxybutyric acid (series A) and alpha-(2-phenylethylamino)-gamma-hydroxybutyric acid (series B), were investigated in maximal electroshock (MES), subcutaneous metrazole, and rotorod toxicity assays. The most,potent anticonvulsant compounds were alpha-(benzylamino)-gamma-hydroxybutyric acid N-benzylamide (3) and N-(2-chlorobenzyl-amide (4) with median effective (ED50) doses 63.0 mg/kg and , respectively. alpha-(4-Phenylpiperazinyl-gamma-hydroxy-butyric acid N-(4-methylbenzyl)amide (17) and alpha-(benzylpiperaz-inyl-gamma-hydroxy-butyric acid N-(4-methylbenzyl)amide (18) were also tested for their ability to potentiate [H-3] -muscimol binding and Ifo inhibit [S-35]-TBPS binding (as indices of GABA-A receptor potentiation). Amide 17 exhibited activity at the GABA-A complex which may be the mechanism by which the anticonvulsant effect of this compound is mediated. The N-benzylamides of alpha-(benzylamino)-gamma-hydroxybutyric acid (3-9) were also evaluated for their ability to displace [H-3] nitrendipine from voltage-sensitive calcium channel (VSCC) receptors isolated from rat cortex.

  DOI：

  10.1002/(sici)1521-4184(19995)332:5<167::aid-ardp167>3.0.co;2-n

文献信息

• Synthesis, Physicochemical Properties, Anticonvulsant Activities, and GABA-ergic and Voltage-sensitive Calcium Channel Receptor Affinities of α-SubstitutedN-Benzylamides of γ-Hydroxybutyric Acid Part 4: Search for New Anticonvulsant Compounds
  作者：Barbara Malawska、Katarzyna Kulig、Lucyna Antkiewicz-Michaluk、Richard Porter、Ani Misra、Ian A. Cliffe

  DOI：10.1002/(sici)1521-4184(19995)332:5<167::aid-ardp167>3.0.co;2-n

  日期：1999.5

  In a search for new anticonvulsant compounds, two series of N-benzylamides of alpha-(benzylamino)-gamma-hydroxybutyric acid (series A) and alpha-(2-phenylethylamino)-gamma-hydroxybutyric acid (series B), were investigated in maximal electroshock (MES), subcutaneous metrazole, and rotorod toxicity assays. The most,potent anticonvulsant compounds were alpha-(benzylamino)-gamma-hydroxybutyric acid N-benzylamide (3) and N-(2-chlorobenzyl-amide (4) with median effective (ED50) doses 63.0 mg/kg and , respectively. alpha-(4-Phenylpiperazinyl-gamma-hydroxy-butyric acid N-(4-methylbenzyl)amide (17) and alpha-(benzylpiperaz-inyl-gamma-hydroxy-butyric acid N-(4-methylbenzyl)amide (18) were also tested for their ability to potentiate [H-3] -muscimol binding and Ifo inhibit [S-35]-TBPS binding (as indices of GABA-A receptor potentiation). Amide 17 exhibited activity at the GABA-A complex which may be the mechanism by which the anticonvulsant effect of this compound is mediated. The N-benzylamides of alpha-(benzylamino)-gamma-hydroxybutyric acid (3-9) were also evaluated for their ability to displace [H-3] nitrendipine from voltage-sensitive calcium channel (VSCC) receptors isolated from rat cortex.