Application of Acyl Aminals in Target and Function Oriented Synthesis

酰基缩醛胺在目标和功能定向合成中的应用

• 批准号: 0848299
• 负责人: Paul Floreancig
• 金额: $ 36万
• 依托单位: University of Pittsburgh
• 依托单位国家: 美国
• 项目类别: Standard Grant
• 财政年份: 2009
• 资助国家: 美国
• 起止时间: 2009-03-01 至 2012-02-29
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=0848299&HistoricalAwards=false
• 关键词: Application; Acyl; Aminals; Target; Function

This project will exploit the utility of acyclic N-acyl aminals in a range of important applications. N-Acyl aminals have been prepared through lengthy standard protocols but their availability from nitriles through a recently developed multicomponent reaction allows for access to greater structural diversity than has previously been available. This multicomponent reaction will be applied to the construction of a library of pederin analogs that would be difficult to access through previous approaches in an effort to minimize the toxicity of this potent immunosuppressive and cytotoxic agent. N-Acyl aminals will be used as precursors to N-acyliminium ions in studies that will validate the use of a capillary-based microreactor for rapidly screening the efficiency and mechanism of chiral acid catalyzed reactions. The capacity to design N-acyl aminals that cleave and release biologically active molecules through predictable stimuli will be utilized in the design of new drug delivery vehicles. With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Professor Paul Floreancig of the Department of Chemistry at the University of Pittsburgh. Professor Floreancig's research efforts revolve around the development and mechanistic analysis of new chemical reactions and the synthesis of biologically active molecules. This research will provide new opportunities for efficient syntheses of molecules that have tunable properties. Successful development of these projects will have an impact on lead generation and synthesis in the pharmaceutical and agricultural industries.

该项目将利用无环N-酰基缩胺在一系列重要应用中的效用。 N-酰基缩醛胺已经通过冗长的标准方案制备，但是它们通过最近开发的多组分反应从腈的可用性允许获得比以前可用的更大的结构多样性。 这种多组分反应将被应用于构建pederin类似物的文库，其将难以通过先前的方法获得，以尽量减少这种有效的免疫抑制剂和细胞毒性剂的毒性。 N-酰基缩胺将被用作研究中N-酰基异氰脲酸离子的前体，该研究将验证基于毛细管的微反应器用于快速筛选手性酸催化反应的效率和机理。 设计通过可预测的刺激裂解和释放生物活性分子的N-酰基缩醛的能力将用于设计新的药物递送载体。有了这个奖项，有机和高分子化学计划正在支持匹兹堡大学化学系的Paul Floreancig教授的研究。 Floreancig教授的研究工作围绕着新化学反应的开发和机理分析以及生物活性分子的合成。 这项研究将为高效合成具有可调性质的分子提供新的机会。 这些项目的成功开发将对制药和农业行业的铅生产和合成产生影响。