tert-butoxycarbonyl (4-(4-fluorophenyl)-1H-imidazol-2-yl)methylamine | 1404113-31-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: tert-butoxycarbonyl (4-(4-fluorophenyl)-1H-imidazol-2-yl)methylamine
• 英文别名: tert-butyl N-[[5-(4-fluorophenyl)-1H-imidazol-2-yl]methyl]carbamate
• CAS: 1404113-31-0
• 化学式: C₁₅H₁₈FN₃O₂
• 分子量: 291.325
• InChiKey: ZYLXBUIIXIHSFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  67
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butoxycarbonyl (4-(4-fluorophenyl)-1H-imidazol-2-yl)methylamine 在 三氟乙酸 、 苯酚 作用下， 反应 3.5h， 生成 7-chloro-N-[[4-(4-fluorophenyl)-1H-imidazol-2-yl]methyl]quinolin-4-amine
  参考文献：
  名称：

  Synthesis and antiplasmodial activity of new heteroaryl derivatives of 7-chloro-4-aminoquinoline

  摘要：

  With the aim to investigate the effect of different heterocyclic rings linked to the 4-aminoquinoline nucleus on the antimalarial activity, a set of 7-chloro-N-(heteroaryl)-methyl-4-aminoquinoline and 7-chloro-N-(heteroaryl)-4-aminoquinoline was synthesized and tested in vitro against D-10 (CQ-S) and W-2 (CQ-R) strains of Plasmodium falciparum. All compounds exhibited from moderate to high antiplasmodial activities. The activity was strongly influenced both by the presence of a methylenic group, as a spacer between the 4-aminoquinoline and the heterocyclic ring, and by the presence of a basic head. The most potent molecules inhibited the growth of both CQ-S and CQ-R strains of P. falciparum with IC50 < 30 nM and were not toxic against human endothelial cells. These results confirm that the presence of an heteroaryl moiety in the side chain of 7-chloro-4-aminoquinoline is useful for the design and development of new powerful antimalarial agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.07.040
• 作为产物：
  描述：

  Boc-glycine cesium salt 在 ammonium acetate 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 tert-butoxycarbonyl (4-(4-fluorophenyl)-1H-imidazol-2-yl)methylamine
  参考文献：
  名称：

  Synthesis and antiplasmodial activity of new heteroaryl derivatives of 7-chloro-4-aminoquinoline

  摘要：

  With the aim to investigate the effect of different heterocyclic rings linked to the 4-aminoquinoline nucleus on the antimalarial activity, a set of 7-chloro-N-(heteroaryl)-methyl-4-aminoquinoline and 7-chloro-N-(heteroaryl)-4-aminoquinoline was synthesized and tested in vitro against D-10 (CQ-S) and W-2 (CQ-R) strains of Plasmodium falciparum. All compounds exhibited from moderate to high antiplasmodial activities. The activity was strongly influenced both by the presence of a methylenic group, as a spacer between the 4-aminoquinoline and the heterocyclic ring, and by the presence of a basic head. The most potent molecules inhibited the growth of both CQ-S and CQ-R strains of P. falciparum with IC50 < 30 nM and were not toxic against human endothelial cells. These results confirm that the presence of an heteroaryl moiety in the side chain of 7-chloro-4-aminoquinoline is useful for the design and development of new powerful antimalarial agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.07.040

文献信息

• Design and synthesis of chiral 2 H -chromene- N -imidazolo-amino acid conjugates as aldose reductase inhibitors
  作者：Gudipudi Gopinath、Venu Sankeshi、Shaym perugu、Malini D. Alaparthi、Srinivas Bandaru、Vijay K. Pasala、Prasad Rao Chittineni、G.L.David Krupadanam、Someswar R. Sagurthi

  DOI：10.1016/j.ejmech.2016.08.070

  日期：2016.11

  Aldose reductase (ALR2) inhibitors provide a viable mode to fight against diabetic complications. ALR2 exhibit plasticity in the active site vicinities and possible shifts in the nearby two supporting alpha helices. Therefore, a novel series of amino acid conjugates of chromene-3-imidazoles (13–15) were designed and synthesized based on natural isoflavonoids. The compounds were identified on the basis

  醛糖还原酶（ALR2）抑制剂为对抗糖尿病并发症提供了一种可行的模式。ALR2在活动部位附近表现出可塑性，并且在附近的两个支撑α螺旋中可能发生位移。因此，在天然异黄酮的基础上，设计并合成了一系列新的色烯-3-咪唑（13-15）的氨基酸缀合物。根据光谱数据（1 H NMR，13 C NMR和MS）鉴定化合物，并在体外测试ALR2抑制活性，IC 50值范围为0.031± 0.082μM至4.29±0.55μM。我们的计算机和生化研究证实了15e在对醛还原酶（ALR1）具有高选择指数的合成化合物中，具有最佳的抑制活性。向STZ诱导的大鼠补充15e可以降低血糖水平，并以剂量​​依赖性方式延缓白内障的进展。因此，本研究提供了具有希望的抑制剂以预防或延缓白内障进展的一系列新化合物。
• Synthesis and antiplasmodial activity of new heteroaryl derivatives of 7-chloro-4-aminoquinoline
  作者：Manolo Casagrande、Anna Barteselli、Nicoletta Basilico、Silvia Parapini、Donatella Taramelli、Anna Sparatore

  DOI：10.1016/j.bmc.2012.07.040

  日期：2012.10

  With the aim to investigate the effect of different heterocyclic rings linked to the 4-aminoquinoline nucleus on the antimalarial activity, a set of 7-chloro-N-(heteroaryl)-methyl-4-aminoquinoline and 7-chloro-N-(heteroaryl)-4-aminoquinoline was synthesized and tested in vitro against D-10 (CQ-S) and W-2 (CQ-R) strains of Plasmodium falciparum. All compounds exhibited from moderate to high antiplasmodial activities. The activity was strongly influenced both by the presence of a methylenic group, as a spacer between the 4-aminoquinoline and the heterocyclic ring, and by the presence of a basic head. The most potent molecules inhibited the growth of both CQ-S and CQ-R strains of P. falciparum with IC50 < 30 nM and were not toxic against human endothelial cells. These results confirm that the presence of an heteroaryl moiety in the side chain of 7-chloro-4-aminoquinoline is useful for the design and development of new powerful antimalarial agents. (C) 2012 Elsevier Ltd. All rights reserved.