1-<(1',2'-butadien-4'-yloxy)methyl>-2-<(hydroxyimino)methyl>-3-methylimidazolium chloride | 117982-99-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-<(1',2'-butadien-4'-yloxy)methyl>-2-<(hydroxyimino)methyl>-3-methylimidazolium chloride
• 英文别名: 1-[(1',2'-butadien-4'-yloxy)methyl]-2-[(hydroxyimino)methyl]-3-methylimidazolium chloride；1H-Imidazolium, 1-((2,3-butadienyloxy)methyl)-2-((hydroxyimino)methyl)-3-methyl-, chloride
• CAS: 117982-99-7
• 化学式: C₁₀H₁₄N₃O₂*Cl
• 分子量: 243.693
• InChiKey: NSBJPDWNYWFXNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.56
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  50.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  buta-1,2-dien-4-yl chloromethyl ether 、 1-methyl-1H-imidazole-2-carbaldehyde oxime 以40%的产率得到1-<(1',2'-butadien-4'-yloxy)methyl>-2-<(hydroxyimino)methyl>-3-methylimidazolium chloride
  参考文献：
  名称：

  Quaternary salts of 2-[(hydroxyimino)methyl]imidazole. 3. Synthesis and evaluation of (alkenyloxy)-, (alkynyloxy)-, and (aralykyloxy)methyl quaternarized 2-[(hydroxyimino)methyl]-1-alkylimidazolium halides as reactivators and therapy for soman intoxication

  摘要：

  A series of structurally related monosubstituted 1-[(alkenyloxy)methyl]-, 1-[(alkynyloxy)methyl]-, and 1-[(aralkyloxy)methyl]-2-[(hydroxyimino)methyl]-3-methyli midazolium halides were prepared and evaluated. All new compounds were characterized with respect to (hydroxyimino)methyl acid dissociation constant, nucleophilicity, and octanol-buffer partition coefficient. The alkynyloxy-substituted compounds were also evaluated in vitro with respect to reversible inhibition of human erythrocyte (RBC) acetylcholinesterase (AChE) and kinetics of reactivation of human AChE inhibited by ethyl p-nitrophenyl methylphosphonate (EPMP). In vivo evaluation in mice revealed that coadministration of alkynyloxy-substituted imidazolium compounds with atropine sulfate provided significant protection against a 2 x LD50 challenge of GD. For the alkynyloxy-substituted imidazolium drugs there is a direct relationship between in vitro and in vivo activity: the most potent in vivo compounds against GD proved to be potent in vitro reactivators against EPMP-inhibited human AChE. These results differ from the observations made on the sterically hindered imidazolium compounds (see previous article) and suggest that several antidotal mechanisms of protective action may be applicable for the imidazolium aldoxime family of therapeutics. The ability of the alkynyloxy substituents to provide life-saving protection against GD intoxication was not transferable to the pyridinium or triazolium heteroaromatic ring systems.

  DOI：

  10.1021/jm00122a035