diethyltetradecanediimidoate hydrochloride

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 甲亚胺酸及其衍生物
• 英文名称: diethyltetradecanediimidoate hydrochloride
• 英文别名: Diethyl tetradecanediimidate;hydrochloride；diethyl tetradecanediimidate;hydrochloride
• 化学式: C₁₈H₃₆N₂O₂*ClH
• 分子量: 348.957
• InChiKey: FLNCUZRGSRTJEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.12
• 重原子数：
  23
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  66.2
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyltetradecanediimidoate hydrochloride 在 盐酸 、 三乙胺 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 生成 1,12-bis(imidazolin-2-yl)dodecane
  参考文献：
  名称：

  Compounds with antiparasitic activity and medicines containing same

  摘要：

  这项发明涉及具有抗寄生虫特别是抗疟活性的化合物，其特征在于它们符合一般式(I)。特别适用于具有抗寄生虫活性的化合物。

  公开号：

  US20050176819A1
• 作为产物：
  描述：

  1,12-二氰基十二烷 在 盐酸 作用下， 以 乙醚 、 乙醇 为溶剂， 以82%的产率得到diethyltetradecanediimidoate hydrochloride
  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

文献信息

• US8012985B2
  申请人：——

  公开号：US8012985B2

  公开（公告）日：2011-09-06
• Compounds with antiparasitic activity and medicines containing same
  申请人：Vial Henri

  公开号：US20050176819A1

  公开（公告）日：2005-08-11

  The invention relates to compounds having an anti-parasitic, in particular antimalarial activity, characterized in that they correspond to general formula (I) Applications in particular as compounds with anti-parasitic activity.

  这项发明涉及具有抗寄生虫特别是抗疟活性的化合物，其特征在于它们符合一般式(I)。特别适用于具有抗寄生虫活性的化合物。
• Potent Antimalarial Activity of 2-Aminopyridinium Salts, Amidines, and Guanidines
  作者：Michèle Calas、Mahama Ouattara、Gilles Piquet、Zyta Ziora、Y. Bordat、Marie L. Ancelin、Roger Escale、Henri Vial

  DOI：10.1021/jm0704752

  日期：2007.12.13

  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.