4,6-Diphenyl-3H-imidazolo[5,4-b]pyridin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4,6-Diphenyl-3H-imidazolo[5,4-b]pyridin-2-one
• 英文别名: 5,7-diphenyl-3H-imidazo[4,5-b]pyridin-2-ol；5,7-diphenyl-1,3-dihydroimidazo[4,5-b]pyridin-2-one
• 化学式: C₁₈H₁₃N₃O
• 分子量: 287.321
• InChiKey: SHTZPAWLYJASHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,6-Diphenyl-3H-imidazolo[5,4-b]pyridin-2-one 、 异丁酸酐 在 异丁酸 、 magnesium chloride 作用下， 反应 10.0h， 以71%的产率得到LUF5980
  参考文献：
  名称：

  2,6,8-Trisubstituted 1-Deazapurines as Adenosine Receptor Antagonists

  摘要：

  In this study we developed a refined pharmacophore model for antagonists of the human adenosine A(1) receptor, based on features of known pyrimidine and purine derivatives. The adoption of these updated criteria assisted us in synthesizing a series of 1-deazapurines with consistently high affinity as inverse agonists for the adenosine A(1) receptor. These 1-deazapurines (otherwise known as 3H-imidazo[4,5-b]pyridines) were substituted at their 2- and 6-positions, yielding a series with five of the derivatives displaying K-i values in the subnanomolar range. The most potent of these, compound 10 (LUF 5978), displayed an affinity of 0.55 nM at the human adenosine A(1) receptor with > 300-fold and 45-fold selectivity toward A(2A) and A(3) receptors, respectively. Compound 14 (LUF 5981, K-i = 0.90 nM) appeared to have the best overall selectivity with respect to adenosine A(2A) (> 200-fold) and A(3) (700-fold) receptors.

  DOI：

  10.1021/jm0607956
• 作为产物：
  描述：

  2-Amino-3-carboxamido-4,6-diphenylpyridine 在 氢氧化钾 、 碘苯二乙酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以52%的产率得到4,6-Diphenyl-3H-imidazolo[5,4-b]pyridin-2-one
  参考文献：
  名称：

  邻氨基苯甲酰胺、水杨酰胺和一些β-取代酰胺的高价碘氧化重排：2-苯并咪唑酮、2-苯并恶唑酮和相关化合物的新型便捷合成

  摘要：

  在甲醇氢氧化钾中用碘苯二乙酸酯氧化邻氨基苯甲酰胺、水杨酰胺和一些β-取代的酰胺，分别导致2-苯并咪唑酮、2-苯并恶唑酮和相关化合物的新且方便的合成。该反应可能通过最初的霍夫曼型重排发生，然后是中间体异氰酸酯的分子内环化。

  DOI：

  10.1055/s-2001-12346

文献信息

• Hypervalent Iodine Oxidative Rearrangement of Anthranilamides, Salicylamides and Some β-Substituted Amides: A New and Convenient Synthesis of 2-Benzimidazolones, 2-Benzoxazolones and Related Compounds
  作者：Om Prakash、Hitesh Batra、Harpreet Kaur、Pawan K. Sharma、Vijay Sharma、Shiv P. Singh、Robert M. Moriarty

  DOI：10.1055/s-2001-12346

  日期：——

  Oxidation of anthranilamides, salicylamides and some b-substituted amides with iodobenzene diacetate in methanolic potassium hydroxide led to a new and convenient synthesis of 2-benzimidazolones, 2-benzoxazolones and related compounds, respectively. The reaction probably occurs via initial Hofmann-type rearrangement followed by intramolecular cyclization of intermediate isocyanate.

  在甲醇氢氧化钾中用碘苯二乙酸酯氧化邻氨基苯甲酰胺、水杨酰胺和一些β-取代的酰胺，分别导致2-苯并咪唑酮、2-苯并恶唑酮和相关化合物的新且方便的合成。该反应可能通过最初的霍夫曼型重排发生，然后是中间体异氰酸酯的分子内环化。
• 2,6,8, Trisubstituted 1-deazapurines and their different uses
  申请人：Chang Lisa Chung Wai

  公开号：US20080139608A1

  公开（公告）日：2008-06-12

  The invention provides a compound having the structure of general formula (I): or a salt thereof, wherein, R represents hydrogen (except when R′=H), halogen, (substituted) alkyl except —CH 3 , (substituted) alkenyl, (substituted) alkynyl, or (substituted) —(CH 2 ) n -aryl; R′ represents hydrogen (except when R=H), halogen, (substituted) alkyl except —CH 3 , (substituted) alkenyl, (substituted) alkynyl, or (substituted) —CH 2 ) n -aryl; R″ represents hydrogen, —(CH 2 ) n -hydroxyl, halogen, acyl, thio-acyl, seleno-acyl, (substituted) alkyl, (substituted) alkenyl, (substituted) alkynyl, or (substituted) —(CH 2 ) n -aryl; and n is a number in the range from 0 to 10. The invention further provides pharmaceutical compositions comprising said compound, and the use of said compound to treat and/or prevent a variety of diseases.

  本发明提供了具有通式（I）的化合物或其盐，其中，R代表氢（除非R′=H），卤素，（取代）烷基（除CH3），（取代）烯基，（取代）炔基或（取代）-（CH2）n-芳基；R′代表氢（除非R=H），卤素，（取代）烷基（除CH3），（取代）烯基，（取代）炔基或（取代）-（CH2）n-芳基；R″代表氢，-（CH2）n-羟基，卤素，酰基，硫酰基，硒酰基，（取代）烷基，（取代）烯基，（取代）炔基或（取代）-（CH2）n-芳基；n为0到10之间的数字。本发明还提供了包含上述化合物的药物组合物，以及使用该化合物治疗和/或预防各种疾病的方法。
• 2,6,8-Trisubstituted 1-Deazapurines as Adenosine Receptor Antagonists
  作者：Lisa C. W. Chang、Jacobien K. von Frijtag Drabbe Künzel、Thea Mulder-Krieger、Joost Westerhout、Thomas Spangenberg、Johannes Brussee、Adriaan P. IJzerman

  DOI：10.1021/jm0607956

  日期：2007.2.1

  In this study we developed a refined pharmacophore model for antagonists of the human adenosine A(1) receptor, based on features of known pyrimidine and purine derivatives. The adoption of these updated criteria assisted us in synthesizing a series of 1-deazapurines with consistently high affinity as inverse agonists for the adenosine A(1) receptor. These 1-deazapurines (otherwise known as 3H-imidazo[4,5-b]pyridines) were substituted at their 2- and 6-positions, yielding a series with five of the derivatives displaying K-i values in the subnanomolar range. The most potent of these, compound 10 (LUF 5978), displayed an affinity of 0.55 nM at the human adenosine A(1) receptor with > 300-fold and 45-fold selectivity toward A(2A) and A(3) receptors, respectively. Compound 14 (LUF 5981, K-i = 0.90 nM) appeared to have the best overall selectivity with respect to adenosine A(2A) (> 200-fold) and A(3) (700-fold) receptors.