1-(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenyl)ethanamine | 1240793-28-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenyl)ethanamine
• 英文别名: 1-[4-[3-(Trifluoromethyl)diazirin-3-yl]phenyl]ethanamine
• CAS: 1240793-28-5
• 化学式: C₁₀H₁₀F₃N₃
• 分子量: 229.205
• InChiKey: GWQRPHFGHPOSHR-UHFFFAOYSA-N

物化性质

• 沸点：
  264.4±50.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenyl)ethanamine 、 氯乙酸乙酯 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以81%的产率得到ethyl 2-(1-(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenyl)ethylamino)ethanoate
  参考文献：
  名称：

  p-Trifluoromethyldiazirinyl-etomidate: A Potent Photoreactive General Anesthetic Derivative of Etomidate That Is Selective for Ligand-Gated Cationic Ion Channels

  摘要：

  We synthesized the R- and S-enantiomers of ethyl 1-(1-(4-(3-((trilluoromethyl)-3H-diazirin-3-yl)-phenyl)ethyl)-1H-imidazole-5-carboxylate (trifluoromethyldiazirinyl-etomidate), or TFD-etomidate, a novel photoactivable derivative of the stereoselective general anesthetic etomidate (R-(2-ethyl 1-(phenylethyl)-1H-imidazole-5-carboxylate)). Anesthetic potency was similar to etomidate's, but stereoselectivity was reversed and attenuated. Relative to etomidate, TFD-etomidate was a more potent inhibitor of the excitatory receptors, nAChR (nicotinic acetylcholine receptor) ((alpha 1)(2)beta 1 delta 1 gamma 1) and 5-HT3AR (serotonin type 3A receptor), causing significant inhibition at anesthetic concentrations. S- but not R-TFD-etomiclate enhanced currents elicited from inhibitory alpha 1 beta 2 gamma 2L GABA(A) Rs by low concentrations of GABA, but with a lower efficacy than R-etomidate, and site-directed mutagenesis suggests they act at different sites. [H-3]TFD-etomidate photolabeled the alpha-subunit of the nAChR in a manner allosterically regulated by agonists and noncompetitive inhibitors. TFD-etomidate's novel pharmacology is unlike that of etomidate derivatives with photoactivable groups in the ester position, which behave like etomidate, suggesting that it will further enhance our understanding of anesthetic mechanisms.

  DOI：

  10.1021/jm100498u
• 作为产物：
  描述：

  3-(4-(1-bromoethyl)phenyl)-3-(trifluoromethyl)-3H-diazirine 在 氨 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以2.1 g的产率得到1-(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenyl)ethanamine
  参考文献：
  名称：

  p-Trifluoromethyldiazirinyl-etomidate: A Potent Photoreactive General Anesthetic Derivative of Etomidate That Is Selective for Ligand-Gated Cationic Ion Channels

  摘要：

  We synthesized the R- and S-enantiomers of ethyl 1-(1-(4-(3-((trilluoromethyl)-3H-diazirin-3-yl)-phenyl)ethyl)-1H-imidazole-5-carboxylate (trifluoromethyldiazirinyl-etomidate), or TFD-etomidate, a novel photoactivable derivative of the stereoselective general anesthetic etomidate (R-(2-ethyl 1-(phenylethyl)-1H-imidazole-5-carboxylate)). Anesthetic potency was similar to etomidate's, but stereoselectivity was reversed and attenuated. Relative to etomidate, TFD-etomidate was a more potent inhibitor of the excitatory receptors, nAChR (nicotinic acetylcholine receptor) ((alpha 1)(2)beta 1 delta 1 gamma 1) and 5-HT3AR (serotonin type 3A receptor), causing significant inhibition at anesthetic concentrations. S- but not R-TFD-etomiclate enhanced currents elicited from inhibitory alpha 1 beta 2 gamma 2L GABA(A) Rs by low concentrations of GABA, but with a lower efficacy than R-etomidate, and site-directed mutagenesis suggests they act at different sites. [H-3]TFD-etomidate photolabeled the alpha-subunit of the nAChR in a manner allosterically regulated by agonists and noncompetitive inhibitors. TFD-etomidate's novel pharmacology is unlike that of etomidate derivatives with photoactivable groups in the ester position, which behave like etomidate, suggesting that it will further enhance our understanding of anesthetic mechanisms.

  DOI：

  10.1021/jm100498u

文献信息

• <i>p</i>-Trifluoromethyldiazirinyl-etomidate: A Potent Photoreactive General Anesthetic Derivative of Etomidate That Is Selective for Ligand-Gated Cationic Ion Channels
  作者：S. Shaukat Husain、Deirdre Stewart、Rooma Desai、Ayman K. Hamouda、S. Guo-Dong Li、Elizabeth Kelly、Zuzana Dostalova、Xiaojuan Zhou、Joseph F. Cotten、Douglas E. Raines、Richard W. Olsen、Jonathan B. Cohen、Stuart A. Forman、Keith W. Miller

  DOI：10.1021/jm100498u

  日期：2010.9.9

  We synthesized the R- and S-enantiomers of ethyl 1-(1-(4-(3-((trilluoromethyl)-3H-diazirin-3-yl)-phenyl)ethyl)-1H-imidazole-5-carboxylate (trifluoromethyldiazirinyl-etomidate), or TFD-etomidate, a novel photoactivable derivative of the stereoselective general anesthetic etomidate (R-(2-ethyl 1-(phenylethyl)-1H-imidazole-5-carboxylate)). Anesthetic potency was similar to etomidate's, but stereoselectivity was reversed and attenuated. Relative to etomidate, TFD-etomidate was a more potent inhibitor of the excitatory receptors, nAChR (nicotinic acetylcholine receptor) ((alpha 1)(2)beta 1 delta 1 gamma 1) and 5-HT3AR (serotonin type 3A receptor), causing significant inhibition at anesthetic concentrations. S- but not R-TFD-etomiclate enhanced currents elicited from inhibitory alpha 1 beta 2 gamma 2L GABA(A) Rs by low concentrations of GABA, but with a lower efficacy than R-etomidate, and site-directed mutagenesis suggests they act at different sites. [H-3]TFD-etomidate photolabeled the alpha-subunit of the nAChR in a manner allosterically regulated by agonists and noncompetitive inhibitors. TFD-etomidate's novel pharmacology is unlike that of etomidate derivatives with photoactivable groups in the ester position, which behave like etomidate, suggesting that it will further enhance our understanding of anesthetic mechanisms.