N,N-diethyl-N'-(tritylcarbamothioyl)acetimidamide | 1173243-36-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N,N-diethyl-N'-(tritylcarbamothioyl)acetimidamide
• 英文别名: N,N-diethyl-N′-(tritylcarbamothioyl)acetimidamide；1-[1-(Diethylamino)ethylidene]-3-tritylthiourea；1-[1-(diethylamino)ethylidene]-3-tritylthiourea
• CAS: 1173243-36-1
• 化学式: C₂₆H₂₉N₃S
• 分子量: 415.602
• InChiKey: HNFSEUCPCIJDFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 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,N-diethyl-N'-(tritylcarbamothioyl)acetimidamide 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 4.0h， 生成
  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-diethylacetamidine 、 异硫氰酸三苯基甲基酯 以 四氢呋喃 为溶剂， 以70%的产率得到N,N-diethyl-N'-(tritylcarbamothioyl)acetimidamide
  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

• A convenient synthesis of di- and trisubstituted 2-aminoimidazoles from 1-amidino-3-trityl-thioureas
  作者：Jitendra C. Kaila、Arshi B. Baraiya、Amit N. Pandya、Hitesh B. Jalani、Kamala K. Vasu、V. Sudarsanam

  DOI：10.1016/j.tetlet.2009.04.083

  日期：2009.7

  Convenient synthesis of 2-amino-1,5-disubstituted and 2-amino-1,4,5-trisubstituted imidazoles has been reported using readily available starting materials and simple reagents under mild conditions. Guanylation of 1-amidino-3-trityl-thioureas 1 and 7 using mercury(II) chloride (Caution) as a thiophile resulted in corresponding guanidines 2 and 8 which on reaction with alpha-bromo ketones yielded 2-tritylaminoimidazoles. Deprotection of 2-tritylaminoimidazoles using trifluoroacetic acid at room temperature furnished desired 2-aminoimidazoles 4 and 10 in good to moderate yields. (C) 2009 Elsevier Ltd. All rights reserved.
• Investigations on substituted (2-aminothiazol-5-yl)(imidazo[1,2-a]pyridin-3-yl)methanones 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.bmc.2021.116091

  日期：2021.4
• 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.