2-carbamoyl-3-methyl-1-<<(3'-methyl-3'-nitrobutyl-2')oxy>methyl>imidazolium chloride | 132567-12-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-carbamoyl-3-methyl-1-<<(3'-methyl-3'-nitrobutyl-2')oxy>methyl>imidazolium chloride
• 英文别名: 1-Methyl-3-[(3-methyl-3-nitrobutan-2-yl)oxymethyl]imidazol-1-ium-2-carboxamide;chloride
• CAS: 132567-12-5
• 化学式: C₁₁H₁₉N₄O₄*Cl
• 分子量: 306.749
• InChiKey: DAWSWJGLABQKLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.17
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-甲基咪唑-2-甲酰胺 、 2-(chloromethoxy)-3-methyl-3-nitrobutane 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 以36%的产率得到2-carbamoyl-3-methyl-1-<<(3'-methyl-3'-nitrobutyl-2')oxy>methyl>imidazolium chloride
  参考文献：
  名称：

  Quaternary salts of 2-[(hydroxyimino)methyl]imidazole. 5. Structure-activity relationships for side-chain nitro-, sulfone-, amino-, and aminosulfonyl-substituted analogs for therapy against anticholinesterase intoxication

  摘要：

  Several quaternary imidazolium oxime derivatives incorporating side chains bearing nitro, sulfone, amino, and aminosulfonyl substituents were prepared and evaluated as treatment therapeutics for anti-AChE intoxication. In vivo test results in the mouse revealed that many of these compounds are highly effective in providing life-saving protection against the extremely toxic cholinesterase inhibitors soman and tabun. Several structure-activity relationships were noted that were characteristic of the side-chain substituent. In vivo test results for additional selected derivatives of some of the more therapeutically active compounds indicated that the quaternary heteroaryl nucleus is essential for activity whereas a nucleophilic moiety (i.e., oxime) is not. In support of previous suspicions, these results afforded additional evidence suggesting that reactivation is not the main mode of antidotal action by the imidazolium oximes. An alternative antidotal mechanism is postulated that is consistent with all data and that involves enzyme protection by the compounds.

  DOI：

  10.1021/jm00108a020

文献信息

• Quaternary salts of 2-[(hydroxyimino)methyl]imidazole. 5. Structure-activity relationships for side-chain nitro-, sulfone-, amino-, and aminosulfonyl-substituted analogs for therapy against anticholinesterase intoxication
  作者：Gary A. Koolpe、Steven M. Lovejoy、Dane A. Goff、Kuei Ying Lin、Doris S. Leung、Clifford D. Bedford、Ralph N. Harris、H. A. Musallam、Irwin Koplovitz

  DOI：10.1021/jm00108a020

  日期：1991.4

  Several quaternary imidazolium oxime derivatives incorporating side chains bearing nitro, sulfone, amino, and aminosulfonyl substituents were prepared and evaluated as treatment therapeutics for anti-AChE intoxication. In vivo test results in the mouse revealed that many of these compounds are highly effective in providing life-saving protection against the extremely toxic cholinesterase inhibitors soman and tabun. Several structure-activity relationships were noted that were characteristic of the side-chain substituent. In vivo test results for additional selected derivatives of some of the more therapeutically active compounds indicated that the quaternary heteroaryl nucleus is essential for activity whereas a nucleophilic moiety (i.e., oxime) is not. In support of previous suspicions, these results afforded additional evidence suggesting that reactivation is not the main mode of antidotal action by the imidazolium oximes. An alternative antidotal mechanism is postulated that is consistent with all data and that involves enzyme protection by the compounds.