N'-((4-chlorophenyl)carbamothioyl)-N,N-dimethylformimidamide | 73161-60-1

• 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'-((4-chlorophenyl)carbamothioyl)-N,N-dimethylformimidamide
• 英文别名: 1-(4-Chlorophenyl)-3-[(dimethylamino)methylidene]thiourea；1-(4-chlorophenyl)-3-(dimethylaminomethylidene)thiourea
• CAS: 73161-60-1
• 化学式: C₁₀H₁₂ClN₃S
• 分子量: 241.744
• InChiKey: RHZZAPBYVAKUFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,3-双(溴甲基)喹喔啉 、 N'-((4-chlorophenyl)carbamothioyl)-N,N-dimethylformimidamide 在 trialkylamine 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以81%的产率得到5,5'-(quinoxaline-2,3-diyl)bis(N-(4-chlorophenyl)thiazol-2-amine)
  参考文献：
  名称：

  Pharmacological investigation of quinoxaline-bisthiazoles as multitarget-directed ligands for the treatment of Alzheimer’s disease

  摘要：

  Alzheimer's disease (AD) is the most prevalent disease of old age leading to dementia. Complex AD pathogenesis involves multiple factors viz. amyloid plaque formation, neurofibrillary tangles and inflammation. Herein we report of a new series of quinoxaline-bisthiazoles as multitarget-directed ligands (MTDLs) targeting BACE-1 and inflammation concurrently. Virtual screening of a library of novel quinoxaline-bisthiazoles was performed by docking studies. The most active molecules from the docking library were taken up for synthesis and characterized by spectral data. Compounds 8a-8n showed BACE-1 inhibition in micro molar range. One of the compounds, 8n showed BACE-1 inhibition at IC50 of 3 +/- 0.07 mu M. Rat paw edema inhibition in acute and chronic models of inflammation were obtained at 69 +/- 0.45% and 55 +/- 0.7%, respectively. Compound 8n also showed noteworthy results in AlCl3 induced AD model. The treated rats exhibited excellent antiamnesic, antiamyloid, antioxidant, and neuroprotective properties. Behavioural parameters suggested improved cognitive functions which further validates the testimony of present study. Moreover, compound 8n was found to have inherent gastrointestinal safety. This new string of quinoxaline-bisthiazoles were identified as effective lead for the generation of potent MTDLs and compound 8n was found to showcase qualities to tackle AD pathogenesis.

  DOI：

  10.1016/j.bioorg.2019.102992
• 作为产物：
  描述：

  N,N-二甲基甲酰胺二甲基缩醛 、 4-氯苯基硫脲 以 甲醇 为溶剂， 以73%的产率得到N'-((4-chlorophenyl)carbamothioyl)-N,N-dimethylformimidamide
  参考文献：
  名称：

  Pharmacological investigation of quinoxaline-bisthiazoles as multitarget-directed ligands for the treatment of Alzheimer’s disease

  摘要：

  Alzheimer's disease (AD) is the most prevalent disease of old age leading to dementia. Complex AD pathogenesis involves multiple factors viz. amyloid plaque formation, neurofibrillary tangles and inflammation. Herein we report of a new series of quinoxaline-bisthiazoles as multitarget-directed ligands (MTDLs) targeting BACE-1 and inflammation concurrently. Virtual screening of a library of novel quinoxaline-bisthiazoles was performed by docking studies. The most active molecules from the docking library were taken up for synthesis and characterized by spectral data. Compounds 8a-8n showed BACE-1 inhibition in micro molar range. One of the compounds, 8n showed BACE-1 inhibition at IC50 of 3 +/- 0.07 mu M. Rat paw edema inhibition in acute and chronic models of inflammation were obtained at 69 +/- 0.45% and 55 +/- 0.7%, respectively. Compound 8n also showed noteworthy results in AlCl3 induced AD model. The treated rats exhibited excellent antiamnesic, antiamyloid, antioxidant, and neuroprotective properties. Behavioural parameters suggested improved cognitive functions which further validates the testimony of present study. Moreover, compound 8n was found to have inherent gastrointestinal safety. This new string of quinoxaline-bisthiazoles were identified as effective lead for the generation of potent MTDLs and compound 8n was found to showcase qualities to tackle AD pathogenesis.

  DOI：

  10.1016/j.bioorg.2019.102992

文献信息

• Synthesis of Functionally Substituted 1,3-Diaza-1,3-butadienes
  作者：S. N. Mazumdar、M. P. Mahajan

  DOI：10.1055/s-1990-26892

  日期：——

  Three methods for the synthesis of various stable 1,3-diaza-1,3-butadienes from easily available thiourea derivatives are reported.

  报道了三种从易得的硫脲衍生物合成各种稳定的1,3-二氮-1,3-丁二烯的方法。
• Pharmacological investigation of quinoxaline-bisthiazoles as multitarget-directed ligands for the treatment of Alzheimer’s disease
  作者：Sneha R. Sagar、Devendra Pratap Singh、Rajesh D. Das、Nirupa B. Panchal、Vasudevan Sudarsanam、Manish Nivsarkar、Kamala K. Vasu

  DOI：10.1016/j.bioorg.2019.102992

  日期：2019.8

  Alzheimer's disease (AD) is the most prevalent disease of old age leading to dementia. Complex AD pathogenesis involves multiple factors viz. amyloid plaque formation, neurofibrillary tangles and inflammation. Herein we report of a new series of quinoxaline-bisthiazoles as multitarget-directed ligands (MTDLs) targeting BACE-1 and inflammation concurrently. Virtual screening of a library of novel quinoxaline-bisthiazoles was performed by docking studies. The most active molecules from the docking library were taken up for synthesis and characterized by spectral data. Compounds 8a-8n showed BACE-1 inhibition in micro molar range. One of the compounds, 8n showed BACE-1 inhibition at IC50 of 3 +/- 0.07 mu M. Rat paw edema inhibition in acute and chronic models of inflammation were obtained at 69 +/- 0.45% and 55 +/- 0.7%, respectively. Compound 8n also showed noteworthy results in AlCl3 induced AD model. The treated rats exhibited excellent antiamnesic, antiamyloid, antioxidant, and neuroprotective properties. Behavioural parameters suggested improved cognitive functions which further validates the testimony of present study. Moreover, compound 8n was found to have inherent gastrointestinal safety. This new string of quinoxaline-bisthiazoles were identified as effective lead for the generation of potent MTDLs and compound 8n was found to showcase qualities to tackle AD pathogenesis.
• A study on synthesis, antioxidant, anticancer activities and docking study of novel benzimidazoloyl thiazole derivatives
  作者：Chithra、Brindha、Mariappan、Simon, Turibius、Abbs Fen Reji

  DOI：10.56042/ijc.v62i6.2514

  日期：——