5-(4-(benzyloxy)phenyl)-3-(4-chlorophenyl)-1-thiocarbamoyl-4,5-dihydro-1H-pyrazole | 1187024-08-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(4-(benzyloxy)phenyl)-3-(4-chlorophenyl)-1-thiocarbamoyl-4,5-dihydro-1H-pyrazole
• 英文别名: 5-(4-Chlorophenyl)-3-(4-phenylmethoxyphenyl)-3,4-dihydropyrazole-2-carbothioamide
• CAS: 1187024-08-3
• 化学式: C₂₃H₂₀ClN₃OS
• 分子量: 421.95
• InChiKey: FCLQSASNCVZGKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  82.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(4-(benzyloxy)phenyl)-3-(4-chlorophenyl)-1-thiocarbamoyl-4,5-dihydro-1H-pyrazole 、 溴乙酸乙酯 以 乙醇 为溶剂， 反应 1.0h， 以51%的产率得到2-(5-(4-(benzyloxy)phenyl)-3-(4-chlorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4(5H)-one
  参考文献：
  名称：

  Synthesis and antiviral activity of new pyrazole and thiazole derivatives

  摘要：

  New N-acetyl (5-8) and N-thiocarbamoyl (9-12) derivatives of 4,5-dihydropyrazole were synthesized starting from alpha,beta-unsaturated ketones under the effect of hydrazine hydrate and thiosemicarbazide, respectively. N-Thiocarbamoylpyrazole derivatives (9-12) were cyclized using either ethyl bromoacetate or phenacyl bromides to afford the novel pyrazolothiazol-4(5H)-ones (13-16) or pyrazolothiazoles (1724). The antiviral activity for such novel compounds against a broad panel of viruses in different cell cultures revealed that N-acetyl 4,5-dihydropyrazole 7 was the only active one at subtoxic concentrations against vaccinia virus (Lederle strain) in HEL cell cultures with a 50% effective concentration (EC(50)) value of 7 mu g/ml. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.03.038
• 作为产物：
  描述：

  3-(4-(benzyloxy)phenyl)-1-(4-chlorophenyl)prop-2-en-1-one 、 氨基硫脲 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以45%的产率得到5-(4-(benzyloxy)phenyl)-3-(4-chlorophenyl)-1-thiocarbamoyl-4,5-dihydro-1H-pyrazole
  参考文献：
  名称：

  Synthesis and antiviral activity of new pyrazole and thiazole derivatives

  摘要：

  New N-acetyl (5-8) and N-thiocarbamoyl (9-12) derivatives of 4,5-dihydropyrazole were synthesized starting from alpha,beta-unsaturated ketones under the effect of hydrazine hydrate and thiosemicarbazide, respectively. N-Thiocarbamoylpyrazole derivatives (9-12) were cyclized using either ethyl bromoacetate or phenacyl bromides to afford the novel pyrazolothiazol-4(5H)-ones (13-16) or pyrazolothiazoles (1724). The antiviral activity for such novel compounds against a broad panel of viruses in different cell cultures revealed that N-acetyl 4,5-dihydropyrazole 7 was the only active one at subtoxic concentrations against vaccinia virus (Lederle strain) in HEL cell cultures with a 50% effective concentration (EC(50)) value of 7 mu g/ml. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.03.038

文献信息

• Synthesis and antiviral activity of new pyrazole and thiazole derivatives
  作者：Osama I. El-Sabbagh、Mohamed M. Baraka、Samy M. Ibrahim、Christophe Pannecouque、Graciela Andrei、Robert Snoeck、Jan Balzarini、Adel A. Rashad

  DOI：10.1016/j.ejmech.2009.03.038

  日期：2009.9

  New N-acetyl (5-8) and N-thiocarbamoyl (9-12) derivatives of 4,5-dihydropyrazole were synthesized starting from alpha,beta-unsaturated ketones under the effect of hydrazine hydrate and thiosemicarbazide, respectively. N-Thiocarbamoylpyrazole derivatives (9-12) were cyclized using either ethyl bromoacetate or phenacyl bromides to afford the novel pyrazolothiazol-4(5H)-ones (13-16) or pyrazolothiazoles (1724). The antiviral activity for such novel compounds against a broad panel of viruses in different cell cultures revealed that N-acetyl 4,5-dihydropyrazole 7 was the only active one at subtoxic concentrations against vaccinia virus (Lederle strain) in HEL cell cultures with a 50% effective concentration (EC(50)) value of 7 mu g/ml. (C) 2009 Elsevier Masson SAS. All rights reserved.