4-Amino-2-pyridin-4-ylphenol | 365532-56-5

• 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-Amino-2-pyridin-4-ylphenol
• CAS: 365532-56-5
• 化学式: C₁₁H₁₀N₂O
• 分子量: 186.213
• InChiKey: XGPGWVKVNZWDQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Amino-2-pyridin-4-ylphenol 在 盐酸 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 生成 4-[(7-Chloroquinolin-4-yl)amino]-2-(diethylaminomethyl)-6-pyridin-4-ylphenol
  参考文献：
  名称：

  Antimalarial drugs. 60. Synthesis, antimalarial activity, and quantitative structure-activity relationships of tebuquine and a series of related 5-[(7-chloro-4-quinolinyl)amino]-3-[(alkylamino)methyl][1,1'-biphenyl]-2-ols and N.omega.-oxides

  摘要：

  A series of 5-[(7-chloro-4-quinolinyl)amino]-3-[(alkylamino)methyl] [1,1'-biphenyl]-2-ols and N omega-oxides was prepared from the substituted 1-phenyl-2-propanones proceeding through the 5-nitro[1,1'-biphenyl]-2-ols, the corresponding amino, and acetamido derivatives to the N-[5-[(alkylamino)methyl]-6-hydroxy[1,1'-biphenyl]-3-yl]acetamides and final condensation with 4,7-dichloroquinoline or the N-oxide. In a quantitative structure-activity relationship study first run on 28 and later expanded to 40 substituted phenyl analogues and their N omega-oxides, increasing antimalarial potency vs. Plasmodium berghei in mice was found to be correlated with decreasing size (sigma MR) and electron donation (sigma sigma) of the phenyl ring substituents. A significant correlation with N omega-oxidation could not be demonstrated. Initial high activity against P. berghei infections in mice led to expanded studies that demonstrated in addition excellent activity against resistant strains of parasite, activity in primate models, and pharmacokinetic properties apparently allowing protection against infection for extended periods of time even after oral administration. Such properties encourage the clinical trial of a member of this class in man.

  DOI：

  10.1021/jm00156a009
• 作为产物：
  描述：

  1-(4-吡啶基)丙酮 在 镍 sodium hydroxide 、 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 20.0h， 生成 4-Amino-2-pyridin-4-ylphenol
  参考文献：
  名称：

  Antimalarial drugs. 60. Synthesis, antimalarial activity, and quantitative structure-activity relationships of tebuquine and a series of related 5-[(7-chloro-4-quinolinyl)amino]-3-[(alkylamino)methyl][1,1'-biphenyl]-2-ols and N.omega.-oxides

  摘要：

  A series of 5-[(7-chloro-4-quinolinyl)amino]-3-[(alkylamino)methyl] [1,1'-biphenyl]-2-ols and N omega-oxides was prepared from the substituted 1-phenyl-2-propanones proceeding through the 5-nitro[1,1'-biphenyl]-2-ols, the corresponding amino, and acetamido derivatives to the N-[5-[(alkylamino)methyl]-6-hydroxy[1,1'-biphenyl]-3-yl]acetamides and final condensation with 4,7-dichloroquinoline or the N-oxide. In a quantitative structure-activity relationship study first run on 28 and later expanded to 40 substituted phenyl analogues and their N omega-oxides, increasing antimalarial potency vs. Plasmodium berghei in mice was found to be correlated with decreasing size (sigma MR) and electron donation (sigma sigma) of the phenyl ring substituents. A significant correlation with N omega-oxidation could not be demonstrated. Initial high activity against P. berghei infections in mice led to expanded studies that demonstrated in addition excellent activity against resistant strains of parasite, activity in primate models, and pharmacokinetic properties apparently allowing protection against infection for extended periods of time even after oral administration. Such properties encourage the clinical trial of a member of this class in man.

  DOI：

  10.1021/jm00156a009

文献信息

• METHOD OF MANUFACTURING BIPYRIDINIUM COMPOUND AND SYNTHETIC INTERMEDIATE OF THE SAME, METHOD OF MANUFACTURING DYE COMPOUND, AND NOVEL BIPYRIDINIUM COMPOUND AND NOVEL DYE COMPOUND COMPRISING THE SAME
  申请人：Nii Kazumi

  公开号：US20090082570A1

  公开（公告）日：2009-03-26

  Provided is a method of manufacturing a bipyridinium compound denoted by general formula (A). In general formula (A), Ar 1 and Ar 2 each independently denote an optionally substituted (hetero)aryl group, R 3 and R 4 each independently denote a substituent that may form a ring with a pyridine ring to which the substituent substitutes, m3 and m4 each independently denote an integer ranging from 0 to 4, X denotes a halogen atom or RSO 3 , and R denotes an optionally substituted aryl group or alkyl group. The method can manufacture a 4,4′-bipyridinium compound under mild reaction conditions in an integrated manner without separation of intermediates.

  提供了一种制造双吡啶化合物的方法，其通用式为(A)。在通用式(A)中，Ar1和Ar2分别独立表示可选择取代的(杂)芳基团，R3和R4分别独立表示可与取代基形成环的基团，m3和m4分别独立表示范围从0到4的整数，X表示卤原子或RSO3，R表示可选择取代的芳基团或烷基团。该方法可以在温和的反应条件下以一体化方式制造4,4'-双吡啶化合物，无需中间体的分离。