N-[(1-methyl-1H-pyrazol-4-yl)carbonyl]-N'-(4-bromophenyl)-thiourea

• 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: N-[(1-methyl-1H-pyrazol-4-yl)carbonyl]-N'-(4-bromophenyl)-thiourea
• 英文别名: N-[(4-bromophenyl)carbamothioyl]-1-methylpyrazole-4-carboxamide
• 化学式: C₁₂H₁₁BrN₄OS
• 分子量: 339.216
• InChiKey: SVPCMNJWZNELQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  91
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[(1-methyl-1H-pyrazol-4-yl)carbonyl]-N'-(4-bromophenyl)-thiourea 在 吡啶 、 水 、 氢溴酸 作用下， 以 丙酮 为溶剂， 反应 1.0h， 生成 N-(3-(4-bromophenyl)-4-methylthiazol-2(3H)-ylidene)-1-methyl-1H-pyrazole-4-carboxamide
  参考文献：
  名称：

  Synthesis and apoptotic activity of new pyrazole derivatives in cancer cell lines

  摘要：

  We designed and synthesized new pyrazole thiourea chimeric derivatives and confirmed their structures by NMR and IR spectra. Apoptotic effects were studied in human cancer cells. The N-[(1-methyl-1H-pyrazol-4-yl)carbonyl]-N'-(3-bromophenyl)-thiourea compound (4b) exhibited the highest apoptosis-inducing effect. Compound 4b and the thiazole derivatives, 5b and 6b, increased the expression of tumor necrosis factor receptors TRAIL-R2 and TRAIL-R1, accompanied by down-modulation of pro-caspase 3 levels, and the augmentation of cleaved caspase 3. They also reduced the levels of apoptosis inhibitory proteins and the expression of the heat-shock proteins Hsp27 and Hsp70. All the tested pyrazole derivatives induced a concentration-dependent increase of cells in G2/M phases. The analysis of the experimental data indicates the reduction of Akt phosphorylation as the most probable cellular mechanism of action for the tested compounds. The in vitro study indicated that compound 4b could be a promising anti-cancer drug, to be further developed in animal models of cancer. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.07.010
• 作为产物：
  描述：

  1-甲基-1H-吡唑-4-羰酰氯 在 PEG-400 作用下， 以 丙酮 为溶剂， 反应 2.0h， 生成 N-[(1-methyl-1H-pyrazol-4-yl)carbonyl]-N'-(4-bromophenyl)-thiourea
  参考文献：
  名称：

  Synthesis and apoptotic activity of new pyrazole derivatives in cancer cell lines

  摘要：

  We designed and synthesized new pyrazole thiourea chimeric derivatives and confirmed their structures by NMR and IR spectra. Apoptotic effects were studied in human cancer cells. The N-[(1-methyl-1H-pyrazol-4-yl)carbonyl]-N'-(3-bromophenyl)-thiourea compound (4b) exhibited the highest apoptosis-inducing effect. Compound 4b and the thiazole derivatives, 5b and 6b, increased the expression of tumor necrosis factor receptors TRAIL-R2 and TRAIL-R1, accompanied by down-modulation of pro-caspase 3 levels, and the augmentation of cleaved caspase 3. They also reduced the levels of apoptosis inhibitory proteins and the expression of the heat-shock proteins Hsp27 and Hsp70. All the tested pyrazole derivatives induced a concentration-dependent increase of cells in G2/M phases. The analysis of the experimental data indicates the reduction of Akt phosphorylation as the most probable cellular mechanism of action for the tested compounds. The in vitro study indicated that compound 4b could be a promising anti-cancer drug, to be further developed in animal models of cancer. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.07.010

文献信息

• Synthesis and apoptotic activity of new pyrazole derivatives in cancer cell lines
  作者：George Mihai Nitulescu、Constantin Draghici、Octavian Tudorel Olaru、Lilia Matei、Aldea Ioana、Laura Denisa Dragu、Coralia Bleotu

  DOI：10.1016/j.bmc.2015.07.010

  日期：2015.9

  We designed and synthesized new pyrazole thiourea chimeric derivatives and confirmed their structures by NMR and IR spectra. Apoptotic effects were studied in human cancer cells. The N-[(1-methyl-1H-pyrazol-4-yl)carbonyl]-N'-(3-bromophenyl)-thiourea compound (4b) exhibited the highest apoptosis-inducing effect. Compound 4b and the thiazole derivatives, 5b and 6b, increased the expression of tumor necrosis factor receptors TRAIL-R2 and TRAIL-R1, accompanied by down-modulation of pro-caspase 3 levels, and the augmentation of cleaved caspase 3. They also reduced the levels of apoptosis inhibitory proteins and the expression of the heat-shock proteins Hsp27 and Hsp70. All the tested pyrazole derivatives induced a concentration-dependent increase of cells in G2/M phases. The analysis of the experimental data indicates the reduction of Akt phosphorylation as the most probable cellular mechanism of action for the tested compounds. The in vitro study indicated that compound 4b could be a promising anti-cancer drug, to be further developed in animal models of cancer. (C) 2015 Elsevier Ltd. All rights reserved.