2-(Hydroxyimino-methyl)-3-methyl-1-[2-(methyl-trifluoromethanesulfonyl-amino)-ethyl]-3H-imidazol-1-ium; chloride | 132567-11-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(Hydroxyimino-methyl)-3-methyl-1-[2-(methyl-trifluoromethanesulfonyl-amino)-ethyl]-3H-imidazol-1-ium; chloride
• 英文别名: 1,1,1-trifluoro-N-[2-[2-[(E)-hydroxyiminomethyl]-3-methylimidazol-3-ium-1-yl]ethyl]-N-methylmethanesulfonamide;chloride
• CAS: 132567-11-4
• 化学式: C₉H₁₄F₃N₄O₃S*Cl
• 分子量: 350.749
• InChiKey: KNJMEUCWMRZSQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.09
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  83.3
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2-<(hydroxyimino)methyl>-1-methylimidazole 、 Trifluoro-methanesulfonic acid 2-(methyl-trifluoromethanesulfonyl-amino)-ethyl ester 在 Amberlite IRA-400 anion (chloride form) 作用下， 生成 2-(Hydroxyimino-methyl)-3-methyl-1-[2-(methyl-trifluoromethanesulfonyl-amino)-ethyl]-3H-imidazol-1-ium; chloride
  参考文献：
  名称：

  Quaternary salts of 2-[(hydroxyimino)methyl]imidazole. 4. Effect of various side-chain substituents on therapeutic activity against anticholinesterase intoxication

  摘要：

  A series of quaternary salt derivatives of 2-[(hydroxyimino)methyl]-1-methylimidazole incorporating various side chains bearing ether, silyl, nitrile, ester, halogen, nitro, sulfone, amino, or aminosulfonyl substituents was prepared and evaluated in vivo for the treatment of anticholinesterase intoxication. Test results in the mouse revealed that the type and location of the side-chain substituent both have a significant influence on the toxicity and antidotal effectiveness of the compounds. Some of the more active examples represent the most potent therapeutics to date against intoxication by the powerful cholinesterase inhibitors soman and tabun. Significantly, the antidotal effectiveness of the compounds was not dependent on the inhibiting agent nor was there any correlation between in vivo efficacy and in vitro reactivation of ethyl (4-nitrophenyl)methylphosphonate inhibited human acetylcholinesterase. These observations suggested that the main mode of antidotal protection by the compounds is something other than enzyme reactivation.

  DOI：

  10.1021/jm00108a019

文献信息

• GOFF, DANE A.;KOOLPE, GARY A.;KELSON, ANDREW B.;VU, HUYNH M.;TAYLOR, DORR+, J. MED. CHEM., 34,(1991) N, C. 1363-1366
  作者：GOFF, DANE A.、KOOLPE, GARY A.、KELSON, ANDREW B.、VU, HUYNH M.、TAYLOR, DORR+

  DOI：——

  日期：——
• Quaternary salts of 2-[(hydroxyimino)methyl]imidazole. 4. Effect of various side-chain substituents on therapeutic activity against anticholinesterase intoxication
  作者：Dane A. Goff、Gary A. Koolpe、Andrew B. Kelson、Huynh M. Vu、Dorris L. Taylor、Clifford D. Bedford、Ralph N. Harris、H. A. Mussalam、Irwin Koplovitz

  DOI：10.1021/jm00108a019

  日期：1991.4

  A series of quaternary salt derivatives of 2-[(hydroxyimino)methyl]-1-methylimidazole incorporating various side chains bearing ether, silyl, nitrile, ester, halogen, nitro, sulfone, amino, or aminosulfonyl substituents was prepared and evaluated in vivo for the treatment of anticholinesterase intoxication. Test results in the mouse revealed that the type and location of the side-chain substituent both have a significant influence on the toxicity and antidotal effectiveness of the compounds. Some of the more active examples represent the most potent therapeutics to date against intoxication by the powerful cholinesterase inhibitors soman and tabun. Significantly, the antidotal effectiveness of the compounds was not dependent on the inhibiting agent nor was there any correlation between in vivo efficacy and in vitro reactivation of ethyl (4-nitrophenyl)methylphosphonate inhibited human acetylcholinesterase. These observations suggested that the main mode of antidotal protection by the compounds is something other than enzyme reactivation.