3-[4-(4-methoxyphenyl)-piperazin-1-yl]-dihydrofuran-2(3H)-one | 1403336-61-7

• 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-[4-(4-methoxyphenyl)-piperazin-1-yl]-dihydrofuran-2(3H)-one
• 英文别名: 3-[4-(4-Methoxyphenyl)piperazin-1-yl]oxolan-2-one
• CAS: 1403336-61-7
• 化学式: C₁₅H₂₀N₂O₃
• 分子量: 276.335
• InChiKey: FEBHFYDZZWKIHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  42
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  α-溴-γ-丁内酯 、 1-(4-甲氧基苯基)哌嗪 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 5.5h， 以67%的产率得到3-[4-(4-methoxyphenyl)-piperazin-1-yl]-dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Search for anticonvulsant and analgesic active derivatives of dihydrofuran-2(3H)-one

  摘要：

  A series of derivatives of dihydrofuran-2(3H)-one (gamma-butyrolactone, GBL) was synthesized and tested for anticonvulsant, neurotoxic and analgesic activity. In the anticonvulsant screening 10 lactones were effective in the maximal electroshock test (MES) at the highest doses (300 and 100 mg/kg, 0.5 h, ip, mice). Statistical analysis showed correlation between the anticonvulsant activity and relative lipophilicity parameters determined by experimental and computational methods (R-M0, ClogP and M log P). Preliminary antinociceptive evaluation of selected derivatives revealed strong analgesic activity. The majority of the tested compounds showed high efficacy in animal models of acute pain (hot plate and writhing tests) and strong local anesthetic activity (modified tail immersion test). The obtained ED50 values were comparable with such analgesics as acetylsalicylic acid and morphine. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.08.037

文献信息

• Search for anticonvulsant and analgesic active derivatives of dihydrofuran-2(3H)-one
  作者：Krzysztof Więckowski、Kinga Sałat、Justyna Bytnar、Marek Bajda、Barbara Filipek、James P. Stables、Barbara Malawska

  DOI：10.1016/j.bmc.2012.08.037

  日期：2012.11

  A series of derivatives of dihydrofuran-2(3H)-one (gamma-butyrolactone, GBL) was synthesized and tested for anticonvulsant, neurotoxic and analgesic activity. In the anticonvulsant screening 10 lactones were effective in the maximal electroshock test (MES) at the highest doses (300 and 100 mg/kg, 0.5 h, ip, mice). Statistical analysis showed correlation between the anticonvulsant activity and relative lipophilicity parameters determined by experimental and computational methods (R-M0, ClogP and M log P). Preliminary antinociceptive evaluation of selected derivatives revealed strong analgesic activity. The majority of the tested compounds showed high efficacy in animal models of acute pain (hot plate and writhing tests) and strong local anesthetic activity (modified tail immersion test). The obtained ED50 values were comparable with such analgesics as acetylsalicylic acid and morphine. (C) 2012 Elsevier Ltd. All rights reserved.