N,N-diethyl-N'-[6-(trifluoromethoxy)benzothiazol-2-yl]acetamidine | 1134963-53-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: N,N-diethyl-N'-[6-(trifluoromethoxy)benzothiazol-2-yl]acetamidine
• 英文别名: N,N-diethyl-N'-[6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]ethanimidamide
• CAS: 1134963-53-3
• 化学式: C₁₄H₁₆F₃N₃OS
• 分子量: 331.362
• InChiKey: OYOOMFPQBRQKHH-UHFFFAOYSA-N

物化性质

• 沸点：
  354.9±52.0 °C(predicted)
• 密度：
  1.30±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  66
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N,N-二乙基乙酰胺 、 利鲁唑 在 三氯氧磷 作用下， 以 甲苯 为溶剂， 反应 3.5h， 以58%的产率得到N,N-diethyl-N'-[6-(trifluoromethoxy)benzothiazol-2-yl]acetamidine
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Amidine, Guanidine, and Thiourea Derivatives of 2-Amino(6-trifluoromethoxy)benzothiazole as Neuroprotective Agents Potentially Useful in Brain Diseases

  摘要：

  A series of amidine, thiourea, and guanidine derivatives of 2-amino-6-(trifluoromethoxy)benzothiazole termed 2, 3, and 4, respectively, and structurally related to riluzole, a neuroprotective drug in many animal models of brain disease, have been synthesized. The biological activity of compounds 2a-e, 3a-f, and 4a,b was preliminarily tested by means of an in vitro protocol of ischemia/reperfusion injury. The results demonstrated that 2c and 3a-d significantly attenuated neuronal injury. Selected for testing of their antioxidant properties, compounds 3a-d were shown to be endowed with a direct ROS scavenging activity. Compounds 3b and 3d were also evaluated for their activity on voltage-dependent Na(+) and Ca(2+) currents in neurons from rat piriform cortex. At 50 mu M, compound 3b inhibited the transient Na(+) Current to a much smaller extent than riluzole, whereas 3d was almost completely ineffective.

  DOI：

  10.1021/jm901375r

文献信息

• Synthesis and Biological Evaluation of Amidine, Guanidine, and Thiourea Derivatives of 2-Amino(6-trifluoromethoxy)benzothiazole as Neuroprotective Agents Potentially Useful in Brain Diseases
  作者：Maurizio Anzini、Alessia Chelini、Alessandra Mancini、Andrea Cappelli、Maria Frosini、Lorenzo Ricci、Massimo Valoti、Jacopo Magistretti、Loretta Castelli、Antonio Giordani、Francesco Makovec、Salvatore Vomero

  DOI：10.1021/jm901375r

  日期：2010.1.28

  A series of amidine, thiourea, and guanidine derivatives of 2-amino-6-(trifluoromethoxy)benzothiazole termed 2, 3, and 4, respectively, and structurally related to riluzole, a neuroprotective drug in many animal models of brain disease, have been synthesized. The biological activity of compounds 2a-e, 3a-f, and 4a,b was preliminarily tested by means of an in vitro protocol of ischemia/reperfusion injury. The results demonstrated that 2c and 3a-d significantly attenuated neuronal injury. Selected for testing of their antioxidant properties, compounds 3a-d were shown to be endowed with a direct ROS scavenging activity. Compounds 3b and 3d were also evaluated for their activity on voltage-dependent Na(+) and Ca(2+) currents in neurons from rat piriform cortex. At 50 mu M, compound 3b inhibited the transient Na(+) Current to a much smaller extent than riluzole, whereas 3d was almost completely ineffective.