2-chloro-4-cyanoimidazole | 1314969-56-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 2-chloro-4-cyanoimidazole
• 英文别名: 2-chloro-1H-imidazole-5-carbonitrile
• CAS: 1314969-56-6
• 化学式: C₄H₂ClN₃
• mdl: MFCD19227559
• 分子量: 127.533
• InChiKey: NDZLYTMETRWCDQ-UHFFFAOYSA-N

物化性质

• 沸点：
  371.6±34.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-溴-1-丁醇 、 2-chloro-4-cyanoimidazole 在 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Artemisinin-indole and artemisinin-imidazole hybrids: Synthesis, cytotoxic evaluation and reversal effects on multidrug resistance in MCF-7/ADR cells

  摘要：

  A series of artemisinin derivatives with MDR reversal activity were designed and synthesized. All hybrids were screened to anticancer activities against four human cancer cell lines (A549, MCF-7, HepG-2, MDA-MB-231) and normal human hepatic cell (L02) in vitro. Most of the new compounds showed higher anticancer activities than artemisinin, among which compounds 11a and 11c displayed superior potency with IC50 6.78 mu M and 5.25 mu M against MCF-7, respectively. The further research indicated that the most potent 11c induced cell cycle arrest at G2 phase in MCF-7. Additionally, compound 11c showed remarkable MDR reversal activity which reversed adriamycin against MCF-7/ADR cells with IC50 0.76 mu M.

  DOI：

  10.1016/j.bmcl.2019.02.021
• 作为产物：
  描述：

  5,8-dimethyltetrazolo[1,5-a]pyrazine 生成 2-chloro-4-cyanoimidazole 、 2-azido-3,6-dimethylpyrazine
  参考文献：
  名称：

  Nitrile Ylides: Allenic and Propargylic Structures from Pyrazinylnitrenes. Experimental and Theoretical Characterization

  摘要：

  Matrix photolysis of 2-pyrazinyl azides/tetrazolo[1,5-a]pyrazines generates nitrile ylides 15 via pyrazinylnitrenes 13 and triazacycloheptatetraenes 14. The nitrile ylides 15 are characterized by IR spectroscopy in conjunction with harmonic and anharmonic vibrational frequency calculations. The nitrile ylides exist in the matrices in the Z,Z-conformations in which they are born. Substitution on the nitrile carbon of nitrile ylides has a profound effect on their structure. Even different conformers of the same molecule can have differences up to 200 cm(-1) in the IR absorptions of the ylide moieties. Nitrite ylides 15a and 15b (R = H or Cl, R' = H) have allenic structures (15 Allenic). Nitrile ylide 15c (R = R' = CH3) has a distinctly propargylic structure (15 Propargylic) in the experimentally observed Z,Z-conformation.

  DOI：

  10.1021/jo500002r

文献信息

• Artemisinin-indole and artemisinin-imidazole hybrids: Synthesis, cytotoxic evaluation and reversal effects on multidrug resistance in MCF-7/ADR cells
  作者：Yanping Hu、Na Li、Jiayao Zhang、Ying Wang、Li Chen、Jianbo Sun

  DOI：10.1016/j.bmcl.2019.02.021

  日期：2019.5

  A series of artemisinin derivatives with MDR reversal activity were designed and synthesized. All hybrids were screened to anticancer activities against four human cancer cell lines (A549, MCF-7, HepG-2, MDA-MB-231) and normal human hepatic cell (L02) in vitro. Most of the new compounds showed higher anticancer activities than artemisinin, among which compounds 11a and 11c displayed superior potency with IC50 6.78 mu M and 5.25 mu M against MCF-7, respectively. The further research indicated that the most potent 11c induced cell cycle arrest at G2 phase in MCF-7. Additionally, compound 11c showed remarkable MDR reversal activity which reversed adriamycin against MCF-7/ADR cells with IC50 0.76 mu M.
• Nitrile Ylides: Allenic and Propargylic Structures from Pyrazinylnitrenes. Experimental and Theoretical Characterization
  作者：Didier Bégué、Chris Addicott、Riko Burgard、Pawel Bednarek、Emilie Guille、Isabelle Baraille、Curt Wentrup

  DOI：10.1021/jo500002r

  日期：2014.3.7

  Matrix photolysis of 2-pyrazinyl azides/tetrazolo[1,5-a]pyrazines generates nitrile ylides 15 via pyrazinylnitrenes 13 and triazacycloheptatetraenes 14. The nitrile ylides 15 are characterized by IR spectroscopy in conjunction with harmonic and anharmonic vibrational frequency calculations. The nitrile ylides exist in the matrices in the Z,Z-conformations in which they are born. Substitution on the nitrile carbon of nitrile ylides has a profound effect on their structure. Even different conformers of the same molecule can have differences up to 200 cm(-1) in the IR absorptions of the ylide moieties. Nitrite ylides 15a and 15b (R = H or Cl, R' = H) have allenic structures (15 Allenic). Nitrile ylide 15c (R = R' = CH3) has a distinctly propargylic structure (15 Propargylic) in the experimentally observed Z,Z-conformation.