N~1~,N~12~-Bis(3,4,5,6-tetrahydro-2H-azepin-7-yl)dodecane-1,12-diamine | 648441-43-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吖庚因类
• 英文名称: N~1~,N~12~-Bis(3,4,5,6-tetrahydro-2H-azepin-7-yl)dodecane-1,12-diamine
• 英文别名: N,N'-bis(3,4,5,6-tetrahydro-2H-azepin-7-yl)dodecane-1,12-diamine
• CAS: 648441-43-4
• 化学式: C₂₄H₄₆N₄
• 分子量: 390.656
• InChiKey: NVXISFLUQDMQBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  28
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  48.8
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-氮杂-2-甲氧基-1-环庚烯 、 1,12-diaminododecane dihydrochloride 以 乙醇 为溶剂， 反应 24.0h， 以72%的产率得到N~1~,N~12~-Bis(3,4,5,6-tetrahydro-2H-azepin-7-yl)dodecane-1,12-diamine
  参考文献：
  名称：

  Potent Antimalarial Activity of 2-Aminopyridinium Salts, Amidines, and Guanidines

  摘要：

  We describe the design, synthesis, and antimalarial activity of 60 bis-tertiary amine, bis-2(1H)-imino-heterocycle, bis-amidine, and bis-guanidine series. Bis-tertiary amines with a linker from 12 to 16 methylene groups were active against the in vitro growth of Plasmodium falciparum within the 10(-6)-10(-7) M concentration range. IC50 decreased by 2 orders of magnitude for bis-2-aminopyridinium salts, bis-amidines, and bis-guanidines (27 compounds with IC50 < 10 nM). Increasing the alkyl chain length from 6 to 12 methylene groups led to increased activity, while beyond this antimalarial activity decreased. Antimalarial activities appear to be strictly related to the basicity of the cationic head with an optimal pK(a) over 12.5. Maximal activity occurs for bis-2-aminopyridinium, two C-duplicated bis-amidines, and three bis-guanidines, with IC50 values lower than 1 nM. In. comparison to similar quaternary ammonium salts, amidinium compounds have distinct structural requirements for antimalarial activity and likely additional binding opportunities on account of their hydrogen-bond-forming properties.

  DOI：

  10.1021/jm0704752