1-(furan-2-carbonyl)-N-(2-(7-methoxynaphthalen-1-yl)ethyl)azetidine-3-carboxamide | 1617524-40-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(furan-2-carbonyl)-N-(2-(7-methoxynaphthalen-1-yl)ethyl)azetidine-3-carboxamide
• 英文别名: 1-(furan-2-carbonyl)-N-[2-(7-methoxynaphthalen-1-yl)ethyl]azetidine-3-carboxamide
• CAS: 1617524-40-9
• 化学式: C₂₂H₂₂N₂O₄
• 分子量: 378.428
• InChiKey: XDFILMNSODWMEH-UHFFFAOYSA-N

物化性质

• 熔点：
  140.1-142.4 °C
• 沸点：
  655.317±55.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.273±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  糠酸（呋喃甲酸） 、 N-(2-(7-methoxynaphthalen-1-yl)ethyl)azetidine-3-carboxamide hydrochloride 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以72%的产率得到1-(furan-2-carbonyl)-N-(2-(7-methoxynaphthalen-1-yl)ethyl)azetidine-3-carboxamide
  参考文献：
  名称：

  Synthesis and biological evaluation of novel naphthalene compounds as potential antidepressant agents

  摘要：

  In this study, a series of novel naphthalene compounds were synthesized and screened for their antidepressant-like activities in vitro and in vivo. Their values for two descriptors (ClogP, tPSA) of the blood brain barrier (BBB) were calculated for early assessment of the central nervous system (CNS) drug-likeness. Seven of them (6d, 6i, 6k, 6o, 6p, 6s and 6t) demonstrated potential protective effects on corticosterone-induced lesion of PC12 cells although they cannot repair the irreversible oxidant injury to PC12 cells by hydrogen peroxide. Compounds with promising neurorestorative activities (6k, 6o and 6p) were further evaluated for their in vivo effects by forced swim test (FST) and open field test (OFT) in C57 mice models. The FST results showed that compounds 6k, 60 and 6p remarkably reduced the immobility time of the tested mice. Among them, compound 6k was the most potent one, much more effective than Agomelatine and comparable to Fluoxetine. The OFT results showed that mice treated with compound 6k traveled a longer distance than those treated with Agomelatine or Fluoxetine, indicating a better general locomotor activity. The paper also proposed a possible binding mode of compound 6k with glucocorticoid receptor by docking study. The in vitro cytotoxicity data on HEK293 and L02 cells suggested compound 6k to be a promising antidepressant candidate for subsequent investigation. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.061

文献信息

• Synthesis and biological evaluation of novel naphthalene compounds as potential antidepressant agents
  作者：Wei Ang、Gong Chen、Li Xiong、Ying Chang、Weiyi Pi、Yuanyuan Liu、Chunlong Li、Jiajia Zheng、Liangxue Zhou、Bo Yang、Yong Deng、Shengyong Yang、Youfu Luo、Yuquan Wei

  DOI：10.1016/j.ejmech.2014.05.061

  日期：2014.7

  In this study, a series of novel naphthalene compounds were synthesized and screened for their antidepressant-like activities in vitro and in vivo. Their values for two descriptors (ClogP, tPSA) of the blood brain barrier (BBB) were calculated for early assessment of the central nervous system (CNS) drug-likeness. Seven of them (6d, 6i, 6k, 6o, 6p, 6s and 6t) demonstrated potential protective effects on corticosterone-induced lesion of PC12 cells although they cannot repair the irreversible oxidant injury to PC12 cells by hydrogen peroxide. Compounds with promising neurorestorative activities (6k, 6o and 6p) were further evaluated for their in vivo effects by forced swim test (FST) and open field test (OFT) in C57 mice models. The FST results showed that compounds 6k, 60 and 6p remarkably reduced the immobility time of the tested mice. Among them, compound 6k was the most potent one, much more effective than Agomelatine and comparable to Fluoxetine. The OFT results showed that mice treated with compound 6k traveled a longer distance than those treated with Agomelatine or Fluoxetine, indicating a better general locomotor activity. The paper also proposed a possible binding mode of compound 6k with glucocorticoid receptor by docking study. The in vitro cytotoxicity data on HEK293 and L02 cells suggested compound 6k to be a promising antidepressant candidate for subsequent investigation. (C) 2014 Elsevier Masson SAS. All rights reserved.