6-chloro-2-(4-fluorophenyl)-1H-imidazo[4,5-b]pyridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-chloro-2-(4-fluorophenyl)-1H-imidazo[4,5-b]pyridine
• 化学式: C₁₂H₇ClFN₃
• 分子量: 247.659
• InChiKey: AHNXHIVHADLLID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,3-二氨基-5-氯吡啶 、 对氟苯甲醛 在 sodium metabisulfite 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以85%的产率得到6-chloro-2-(4-fluorophenyl)-1H-imidazo[4,5-b]pyridine
  参考文献：
  名称：

  Synthesis of 6-chloro-2-Aryl-1H-imidazo[4,5-b]pyridine derivatives: Antidiabetic, antioxidant, β-glucuronidase inhibiton and their molecular docking studies

  摘要：

  6-Chloro-2-Aryl-1H-imidazo[4,5-b]pyridine derivatives 1-26 were synthesized and characterized by various spectroscopic techniques. All these derivatives were evaluated for their antiglycation, antioxidant and beta-glucuronidase potential followed their docking studies. In antiglycation assay, compound 2 (IC50 = 240.10 +/- 2.50 mu M) and 4 (IC50 = 240.30 +/- 2.90 mu M) was found to be most active compound of this series, while compounds 3 (IC50 = 260.10 +/- 2.50 mu M), 6 (IC50 = 290.60 +/- 3.60 mu M), 13 (IC50 = 288.20 +/- 3.00 mu M) and 26 (IC50 = 292.10 +/- 3.20 mu M) also showed better activities than the standard rutin (IC50 = 294.50 +/- 1.50 mu M). In antioxidant assay, compound 1 (IC50 = 69.45 +/- 0.25 mu M), 2 (IC50 = 58.10 +/- 2.50 mu M), 3 (IC50 = 74.25 +/- 1.10 mu M), and 4 (IC50 = 72.50 +/- 3.30 mu M) showed good activities. In beta-glucuronidase activity, compounds 3 (IC50 = 29.25 +/- 0.50 mu M), compound 1 (IC50= 30.10 +/- 0.60 mu M) and compound 4 (IC50 = 46.10 +/- 1.10 mu M) showed a significant activity as compared to than standard D-Saccharic acid 1,4-lactonec (IC50 = 48.50 +/- 1.25 mu M) and their interaction with the enzyme was confirm by docking studies. (C) 2016 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2016.01.007

文献信息

• Nowicka, Anna; Liszkiewicz, Hanna; Nawrocka, Wanda P., Acta poloniae pharmaceutica, 2015, vol. 72, # 1, p. 101 - 111
  作者：Nowicka, Anna、Liszkiewicz, Hanna、Nawrocka, Wanda P.、Wietrzyk, Joanna、Zubiak, Agnieszka、Kołodziejczyk, Wojciech

  DOI：——

  日期：——
• Synthesis of 6-chloro-2-Aryl-1H-imidazo[4,5-b]pyridine derivatives: Antidiabetic, antioxidant, β-glucuronidase inhibiton and their molecular docking studies
  作者：Muhammad Taha、Nor Hadiani Ismail、Syahrul Imran、Hesham Rashwan、Waqas Jamil、Sajjad Ali、Syed Muhammad Kashif、Fazal Rahim、Uzma Salar、Khalid Mohammed Khan

  DOI：10.1016/j.bioorg.2016.01.007

  日期：2016.4

  6-Chloro-2-Aryl-1H-imidazo[4,5-b]pyridine derivatives 1-26 were synthesized and characterized by various spectroscopic techniques. All these derivatives were evaluated for their antiglycation, antioxidant and beta-glucuronidase potential followed their docking studies. In antiglycation assay, compound 2 (IC50 = 240.10 +/- 2.50 mu M) and 4 (IC50 = 240.30 +/- 2.90 mu M) was found to be most active compound of this series, while compounds 3 (IC50 = 260.10 +/- 2.50 mu M), 6 (IC50 = 290.60 +/- 3.60 mu M), 13 (IC50 = 288.20 +/- 3.00 mu M) and 26 (IC50 = 292.10 +/- 3.20 mu M) also showed better activities than the standard rutin (IC50 = 294.50 +/- 1.50 mu M). In antioxidant assay, compound 1 (IC50 = 69.45 +/- 0.25 mu M), 2 (IC50 = 58.10 +/- 2.50 mu M), 3 (IC50 = 74.25 +/- 1.10 mu M), and 4 (IC50 = 72.50 +/- 3.30 mu M) showed good activities. In beta-glucuronidase activity, compounds 3 (IC50 = 29.25 +/- 0.50 mu M), compound 1 (IC50= 30.10 +/- 0.60 mu M) and compound 4 (IC50 = 46.10 +/- 1.10 mu M) showed a significant activity as compared to than standard D-Saccharic acid 1,4-lactonec (IC50 = 48.50 +/- 1.25 mu M) and their interaction with the enzyme was confirm by docking studies. (C) 2016 Elsevier Inc. All rights reserved.