SOLUTION CHEMISTRY OF N-ACETYL-P-BENZOQUINONE IMINE

N-乙酰基-对苯醌亚胺的溶液化学

• 批准号: 3438538
• 负责人: Michael Novak
• 金额: $ 5.91万
• 依托单位: MIAMI UNIVERSITY OXFORD
• 依托单位国家: 美国
• 财政年份: 1987
• 资助国家: 美国
• 起止时间: 1987-07-01 至 1989-12-31
• 项目状态: 已结题
• 来源: https://reporter.nih.gov/project-details/3438538
• 关键词: acetaminophen; analgesics; electron spin resonance spectroscopy; high performance liquid chromatography; hydrolysis; imines; oxidation reduction reaction; quinones; solutions; ultraviolet spectrometry

N-Acetyl-p-benzoquinone imine is an important toxic metabolite of acetaminophen and phenacetin, two common analgesics. Certain ring-substituted derivatives of this material are also toxins. Although there is considerable speculation concerning the mechanism of action of this and related quinone imine derivatives, there is little detailed knowledge of the chemistry of these compounds on which to base such conjectures. We have commenced a study of the chemistry of N-acetyl-p-benzoquinone imine and related compounds. Our study is concerned with the mechanisms of the generation of the quinone imine from its assumed precursors in phenacetin metabolism, its hydrolysis reactions and its reactions with Lewis bases in an aqueous environment, and its redox chemistry. We are employing kinetic methods which involve the use of UV spectrophotometry and HPLC to characterize these reactions. Product studies are also being carried out in an effort to understand the chemistry of this material. We are also using cyclic voltammetry and ESR methods to detect possible radical intermediates that may be involved in its redox reactions. We expect that the results of this study will provide a more sound basis for understanding the in vivo activity of N-acetyl-p- benzoquinone imine, and the ways in which it may be generated in biological systems.

N-乙酰基对苯醌亚胺是一种重要的有毒代谢物 对乙酰氨基酚和非那西丁两种常见的止痛药。 该物质的某些环取代的衍生物也是 毒素 虽然有相当多的猜测， 这一和相关醌亚胺的作用机理 衍生物，很少有详细的化学知识， 这些化合物作为这些结构的基础。 我们有 开始研究N-乙酰基对苯醌的化学性质 亚胺和相关化合物。 我们的研究关注的是 从其生成醌亚胺的机制 假定非那西丁代谢的前体，其水解 反应及其与刘易斯碱的反应 环境及其氧化还原化学。 我们使用动能 涉及使用紫外分光光度法的方法， HPLC来表征这些反应。 产品研究也 正在进行的努力是为了了解其中的化学成分 材料 我们还使用循环伏安法和ESR方法 来检测可能涉及的自由基中间体， 氧化还原反应。 我们预计这项研究的结果将提供更健全的 理解N-乙酰基-p- 苯醌亚胺，以及它可以在 生物系统。