N⁸-(4-amino-1-methylbutyl)-2-(1-adamantyl)-6-methoxy-8-quinolinamine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N⁸-(4-amino-1-methylbutyl)-2-(1-adamantyl)-6-methoxy-8-quinolinamine
• 英文别名: 2-(1-adamantyl)primaquine；N⁸-[4-amino-1-methylbutyl]-2-adamantyl-6-methoxy-8-quinolinamine；4-N-[2-(1-adamantyl)-6-methoxyquinolin-8-yl]pentane-1,4-diamine
• 化学式: C₂₅H₃₅N₃O
• 分子量: 393.572
• InChiKey: APZCHSVFDBPQAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  60.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-金刚烷甲酸 在 镍 ammonium persulfate 、 硫酸 、 氢气 、 一水合肼 、 silver nitrate 、 三乙胺 作用下， 以 乙醇 、 乙腈 为溶剂， 120.0 ℃ 、310.26 kPa 条件下， 反应 32.92h， 生成 N⁸-(4-amino-1-methylbutyl)-2-(1-adamantyl)-6-methoxy-8-quinolinamine
  参考文献：
  名称：

  Discovery of a Bulky 2-tert-Butyl Group Containing Primaquine Analogue That Exhibits Potent Blood-Schizontocidal Antimalarial Activities and Complete Elimination of Methemoglobin Toxicity

  摘要：

  To eliminate an unwarranted metabolic pathway of the quinoline ring, a set of two compounds, where C-2 position of the antimalarial drug primaquine is blocked by metabolically stable bulky alkyl group are synthesized. Compound 2 [R = C(CH3)(3)] of the series has produced excellent antimalarial efficacy against P. berghei and highly virulent multidrug-resistant P. yoelii nigeriensis strain in vivo. Compound 2 was also evaluated for methemoglobin (MetHb) toxicity. This study describes the discovery of a highly potent blood-schizontocidal antimalarial analogue 2, completely devoid of MetHb toxicity.

  DOI：

  10.1021/jm0304562

文献信息

• Discovery of a Bulky 2-<i>tert</i>-Butyl Group Containing Primaquine Analogue That Exhibits Potent Blood-Schizontocidal Antimalarial Activities and Complete Elimination of Methemoglobin Toxicity
  作者：Meenakshi Jain、Suryanarayana Vangapandu、Sandeep Sachdeva、Savita Singh、Prati P. Singh、Gopa B. Jena、Kulbhushan Tikoo、Poduri Ramarao、Chaman L. Kaul、Rahul Jain

  DOI：10.1021/jm0304562

  日期：2004.1.1

  To eliminate an unwarranted metabolic pathway of the quinoline ring, a set of two compounds, where C-2 position of the antimalarial drug primaquine is blocked by metabolically stable bulky alkyl group are synthesized. Compound 2 [R = C(CH3)(3)] of the series has produced excellent antimalarial efficacy against P. berghei and highly virulent multidrug-resistant P. yoelii nigeriensis strain in vivo. Compound 2 was also evaluated for methemoglobin (MetHb) toxicity. This study describes the discovery of a highly potent blood-schizontocidal antimalarial analogue 2, completely devoid of MetHb toxicity.