1-ethyl-3-[(phenyl)-(phenylimino)methyl]thiourea | 70375-40-5

• 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: 1-ethyl-3-[(phenyl)-(phenylimino)methyl]thiourea
• 英文别名: 1-ethyl-3-(phenyl-phenyliminomethyl)thiourea；N-(ethyl-thiocarbamoyl)-N'-phenyl-benzamidine；N-Ethyl-N'-(N-phenylbenzimidoyl)thioharnstoff；1-[Anilino(phenyl)methylidene]-3-ethylthiourea；1-[anilino(phenyl)methylidene]-3-ethylthiourea
• CAS: 70375-40-5
• 化学式: C₁₆H₁₇N₃S
• 分子量: 283.397
• InChiKey: OVUNZMLGRIIIFY-UHFFFAOYSA-N

物化性质

• 熔点：
  133 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  411.2±28.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  68.5
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-ethyl-3-[(phenyl)-(phenylimino)methyl]thiourea 在 溴 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 (2,3-diphenyl-2H-[1,2,4]thiadiazol-5-ylidene)-ethyl-amine
  参考文献：
  名称：

  Goerdeler,J. et al., Chemische Berichte, 1979, vol. 112, p. 1288 - 1296

  摘要：

  DOI：
• 作为产物：
  描述：

  N-苯甲酰替苯胺 在 氯化亚砜 作用下， 以 丙酮 为溶剂， 生成 1-ethyl-3-[(phenyl)-(phenylimino)methyl]thiourea
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 2,3,5-Substituted [1,2,4]Thiadiazoles as Allosteric Modulators of Adenosine Receptors

  摘要：

  A number of 2,3,5-substituted [1,2,4]thiadiazole analogues of SCH-202676 (N-(2,3-diphenyl-[1,2,4]thiadiazole-5(2H)-ylidene)methanamine, 7a) were synthesized and tested as potential allosteric modulators of adenosine receptors. All compounds were capable of displacing the binding of the radiolabeled agonist [H-3]CCPA to human A(1) adenosine receptors, whereas modest and varying effects were observed on the binding of [H-3]DPCPX, a radiolabeled antagonist for this receptor subtype. Four compounds, 7a (SCH-202676), 7k (LUF5792), 71 (LUF5794), and 8e (LUF5789), were selected for more detailed characterization. They all proved allosteric inhibitors of agonist binding, with 7k being most potent, whereas their effects on antagonist binding were more ambiguous. Subsequently, experiments were done on human adenosine A(2A) and A(3) receptors. Compounds 7a and 71 displayed peculiar displacement characteristics of both radiolabeled agonist and antagonist binding to A(2A) receptors, whereas 7a showed some activity on A(3) receptors.

  DOI：

  10.1021/jm030863d

文献信息

• Synthesis and Biological Evaluation of a New Series of 2,3,5-Substituted [1,2,4]-Thiadiazoles as Modulators of Adenosine A₁ Receptors and Their Molecular Mechanism of Action
  作者：Anikó Göblyös、Henk de Vries、Johannes Brussee、Adriaan P. IJzerman

  DOI：10.1021/jm049337s

  日期：2005.2.1

  We synthesized two series (7a-i and 8a-i) of 2,3,5-substituted [1,2,4]-thiadiazole analogues of SCH-202676 (7a, 2,3-diphenyl-5-N-methylimino-2H-[1,2,4]-thiadiazole) with emphasis on the N-imino substituent. Compounds 7a-g,i and 8a-g at a final concentration of 1 muM significantly inhibited [H-3]CCPA (2-chloro-N-6-cyclopentyladenosine) agonist binding to human A, adenosine receptors. At the same concentration, all compounds appeared to increase [3H]DPCPX (1,3-dipropyl-8-cyclopentylxanthine) antagonist binding. Compound 7a and LUF5855 (7g) were selected for further characterization and studied in both equilibrium and kinetic radioligand binding experiments. The results suggest a nonstoichiometric interaction with the receptor. Further bioanalytical procedures (HPLC and MS) provided proof for an unusual receptor interaction in which 7a and 7g upon incubation were transformed into their corresponding thioureas 5a and 5g. We suggest that the thiadiazoles are sulfhydryl modifying agents rather than allosteric modulators, as they appear to reversibly modify the sulfhydryl groups of cysteine residues in cell membrane preparations.
• GOERDELER J.; HAAG J.; LOEBACH W., CHEM. BER., 1979, 112, NO 4, 1288-1296
  作者：GOERDELER J.、 HAAG J.、 LOEBACH W.

  DOI：——

  日期：——
• Synthesis and Biological Evaluation of 2,3,5-Substituted [1,2,4]Thiadiazoles as Allosteric Modulators of Adenosine Receptors
  作者：Adrianus M. C. H. van den Nieuwendijk、Daniele Pietra、Laura Heitman、Anikó Göblyös、Adriaan P. IJzerman

  DOI：10.1021/jm030863d

  日期：2004.1.1

  A number of 2,3,5-substituted [1,2,4]thiadiazole analogues of SCH-202676 (N-(2,3-diphenyl-[1,2,4]thiadiazole-5(2H)-ylidene)methanamine, 7a) were synthesized and tested as potential allosteric modulators of adenosine receptors. All compounds were capable of displacing the binding of the radiolabeled agonist [H-3]CCPA to human A(1) adenosine receptors, whereas modest and varying effects were observed on the binding of [H-3]DPCPX, a radiolabeled antagonist for this receptor subtype. Four compounds, 7a (SCH-202676), 7k (LUF5792), 71 (LUF5794), and 8e (LUF5789), were selected for more detailed characterization. They all proved allosteric inhibitors of agonist binding, with 7k being most potent, whereas their effects on antagonist binding were more ambiguous. Subsequently, experiments were done on human adenosine A(2A) and A(3) receptors. Compounds 7a and 71 displayed peculiar displacement characteristics of both radiolabeled agonist and antagonist binding to A(2A) receptors, whereas 7a showed some activity on A(3) receptors.
• Goerdeler,J. et al., Chemische Berichte, 1979, vol. 112, p. 1288 - 1296
  作者：Goerdeler,J. et al.

  DOI：——

  日期：——