5-(3-bromophenyl)-3-phenyl-4,5-dihydro- 1H-pyrazole-1-carbothioamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(3-bromophenyl)-3-phenyl-4,5-dihydro- 1H-pyrazole-1-carbothioamide
• 英文别名: 1-Thiocarbamoyl-5-(3-bromophenyl)-3-phenyl-4,5-dihydro-1H-pyrazole；5-(3-bromophenyl)-3-phenyl-4,5-dihydro-1H-pyrazole-1-carbothioamide；3-(3-bromophenyl)-5-phenyl-3,4-dihydropyrazole-2-carbothioamide
• 化学式: C₁₆H₁₄BrN₃S
• 分子量: 360.277
• InChiKey: DNABWOABVMGVRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  73.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(溴乙酰基)香豆素 、 5-(3-bromophenyl)-3-phenyl-4,5-dihydro- 1H-pyrazole-1-carbothioamide 以 乙醇 为溶剂， 反应 2.0h， 生成 3-(2-(5-(3-bromophenyl)-3-phenyl-4,5-dihydropyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one
  参考文献：
  名称：

  Synthesis, quantum chemical, in vitro acetyl cholinesterase inhibition and molecular docking studies of four new coumarin based pyrazolylthiazole nuclei

  摘要：

  Four new 3-(2-(3-Phenyl-5-substituted phenyl-4,5-dihydropyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one derivatives (1-4) were synthesized and fully characterized by spectroscopic techniques. The final structures of all chromenone analogues (1-4) were confirmed by single crystal X-ray diffraction analysis. Quantum chemical studies were performed to compare the results from the theoretical studies with the experimental (X-ray as well as spectroscopic) ones. The theoretically simulated geometric parameters and other spectroscopic properties agreed nicely with the experimental data. All compounds were evaluated for biological activity (acetyl cholinesterase inhibition potential). Compound 3 emerged as the most potent derivative in acetylcholine esterase (AChE) inhibition assay with IC50 = 27.29 mu M. The IC50 of compound 3 is greater than the standard drug galantamine (IC50 = 44.02 mu M). To rationalize the potencies, molecular docking studies were also carried out. These docking results revealed a good correlation between binding energies values and in vitro AChE inhibition assay. (C) 2018 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2018.05.017
• 作为产物：
  描述：

  间溴苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 5-(3-bromophenyl)-3-phenyl-4,5-dihydro- 1H-pyrazole-1-carbothioamide
  参考文献：
  名称：

  Synthesis, quantum chemical, in vitro acetyl cholinesterase inhibition and molecular docking studies of four new coumarin based pyrazolylthiazole nuclei

  摘要：

  Four new 3-(2-(3-Phenyl-5-substituted phenyl-4,5-dihydropyrazol-1-yl)thiazol-4-yl)-2H-chromen-2-one derivatives (1-4) were synthesized and fully characterized by spectroscopic techniques. The final structures of all chromenone analogues (1-4) were confirmed by single crystal X-ray diffraction analysis. Quantum chemical studies were performed to compare the results from the theoretical studies with the experimental (X-ray as well as spectroscopic) ones. The theoretically simulated geometric parameters and other spectroscopic properties agreed nicely with the experimental data. All compounds were evaluated for biological activity (acetyl cholinesterase inhibition potential). Compound 3 emerged as the most potent derivative in acetylcholine esterase (AChE) inhibition assay with IC50 = 27.29 mu M. The IC50 of compound 3 is greater than the standard drug galantamine (IC50 = 44.02 mu M). To rationalize the potencies, molecular docking studies were also carried out. These docking results revealed a good correlation between binding energies values and in vitro AChE inhibition assay. (C) 2018 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2018.05.017

文献信息

• Microwave Assisted Synthesis of Thiocarbamoylpyrazoles and Application as an Alternative Latent Fingermark Developers
  作者：Bruno da Rosa、Dalila Venzke、Taís Poletti、Nathalia de Lima、Jeanifer Camacho、Kristiane Mariotti、Marco dos Santos、Lucas Pizzuti、Neftalí Carreño、Claudio Pereira

  DOI：10.21577/0103-5053.20200014

  日期：——

  Fingerprints are unique to each individual, contributing to human identification in forensic cases. The powder technique being widely used is considered one of the most important in latent fingermarks analysis. In this sense, the present work aimed to synthesize 1-thiocarbamoyl-4,5-dihydro-1H-pyrazoles and apply them as powder agents to develop latent fingermarks. The compounds were prepared from an effective and green synthesis via the condensation of chalcones with thiosemicarbazide in ethanol under microwave irradiation. Pyrazoles were tested and compared with a standard white powder (Sirchie (R)) on glass surfaces using sebaceous and natural fingermarks so that molecule 2c has been shown to be more promising providing image clarity. The derivatives of pyrazoles were promising as an alternative latent fingermark, presenting high quality images for fingermarks, proving to be a great tool for forensic sciences.