(E)-N-(2-propynyl)-N'-[2-(4-trifluoromethylphenyl)ethylidene]hydrazine | 1065495-55-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-N-(2-propynyl)-N'-[2-(4-trifluoromethylphenyl)ethylidene]hydrazine
• 英文别名: (E)-N-(2-propynyl)-(2-(4-trifluoromethyl-phenyl)ethylidene)hydrazine；N-[(E)-2-[4-(trifluoromethyl)phenyl]ethylideneamino]prop-2-yn-1-amine
• CAS: 1065495-55-7
• 化学式: C₁₂H₁₁F₃N₂
• 分子量: 240.228
• InChiKey: ZDTLMGVOYBVFEY-RQZCQDPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-丙炔-1-基肼 、 4-三氟甲基苯乙醛 在 1,1-双(2-丙炔基)肼 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (Z)-N-(2-propynyl)-N'-[2-(4-trifluoromethylphenyl)ethylidene]hydrazine 、 (E)-N-(2-propynyl)-N'-[2-(4-trifluoromethylphenyl)ethylidene]hydrazine
  参考文献：
  名称：

  N-Propynyl analogs of β-phenylethylidenehydrazines: Synthesis and evaluation of effects on glycine, GABA, and monoamine oxidase

  摘要：

  A group of beta-phenylethylidenehydrazines possessing a variety of substituents ( Me, OMe, Cl, F, and CF(3)) at the ortho-, meta-, or para- positions of the phenyl ring, in conjunction with either a N-bis-(2-propynyl) or a N-mono-(2-propynyl) moiety, were synthesized and compared to the novel neuroprotective drug beta-phenylethylidenehydrazine (PEH) with regard to their ability to inhibit the enzymes GABA- transaminase ( GABA- T) and monoamine oxidase (MAO)-A and -B in vitro in brain tissue. Two of the analogs synthesized (mono- and bis-N-propynylPEH) were also studied ex vivo in rats to compare their effects to those of PEH with regard to ability to inhibit GABA- T and MAO and to change brain levels of several important amino acids. Unlike PEH, none of the new drugs inhibited GABA- T in vitro at 10 or 100 mu M, and all of the drugs ( including PEH) were poor inhibitors ( at 10 mu M) of MAO-A and -B in vitro. The two analogs studied ex vivo inhibited GABA- T to a lesser extent than PEH, unlike PEH that did not elevate brain levels of GABA, and inhibited MAO-A and -B more potently than PEH. Interestingly, unlike PEH, the two analogs caused marked increases in brain levels of glycine; because of the current interest in drugs that increase glycine availability in the brain as potential antipsychotic drugs, these two analogs now warrant further investigation. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.07.027

文献信息

• N-Propynyl analogs of β-phenylethylidenehydrazines: Synthesis and evaluation of effects on glycine, GABA, and monoamine oxidase
  作者：Erin M. MacKenzie、Afshin Fassihi、Asghar Davood、Qiao-Hong Chen、Gillian Rauw、Gail Rauw、Edward E. Knaus、Glen B. Baker

  DOI：10.1016/j.bmc.2008.07.027

  日期：2008.9

  A group of beta-phenylethylidenehydrazines possessing a variety of substituents ( Me, OMe, Cl, F, and CF(3)) at the ortho-, meta-, or para- positions of the phenyl ring, in conjunction with either a N-bis-(2-propynyl) or a N-mono-(2-propynyl) moiety, were synthesized and compared to the novel neuroprotective drug beta-phenylethylidenehydrazine (PEH) with regard to their ability to inhibit the enzymes GABA- transaminase ( GABA- T) and monoamine oxidase (MAO)-A and -B in vitro in brain tissue. Two of the analogs synthesized (mono- and bis-N-propynylPEH) were also studied ex vivo in rats to compare their effects to those of PEH with regard to ability to inhibit GABA- T and MAO and to change brain levels of several important amino acids. Unlike PEH, none of the new drugs inhibited GABA- T in vitro at 10 or 100 mu M, and all of the drugs ( including PEH) were poor inhibitors ( at 10 mu M) of MAO-A and -B in vitro. The two analogs studied ex vivo inhibited GABA- T to a lesser extent than PEH, unlike PEH that did not elevate brain levels of GABA, and inhibited MAO-A and -B more potently than PEH. Interestingly, unlike PEH, the two analogs caused marked increases in brain levels of glycine; because of the current interest in drugs that increase glycine availability in the brain as potential antipsychotic drugs, these two analogs now warrant further investigation. (C) 2008 Elsevier Ltd. All rights reserved.