College of Agronomy and Biotechnology, China Agricultural University, Beijing 100193, China.
College of Science, China Agricultural University, Beijing 100193, China.
Molecules. 2022 Feb 28;27(5):1596. doi: 10.3390/molecules27051596.
Unsubstituted pyridin-2-amine has a high quantum yield and is a potential scaffold for a fluorescent probe. However, the facile access to conjugated highly substituted aminopyridines and the study of their fluorescent properties is scarce. In this paper, synthesis and fluorescent properties of multisubstituted aminopyridines were studied based on a recently developed Rh-catalyzed coupling of vinyl azide with isonitrile to form a vinyl carbodiimide intermediate, following tandem cyclization with an alkyne. An aminopyridine substituted with an azide group as a potential probe was further designed, synthesized, and evaluated. The "clicking-and-probing" experiment of it on BSA protein showed the potential of aminopyridine as a scaffold of a biological probe.
未取代的吡啶-2-胺具有高量子产率，是荧光探针的潜在支架。然而，易于获得共轭的高度取代的氨基吡啶并研究其荧光性质的方法却很少。本文基于最近开发的 Rh 催化的乙烯基叠氮化物与异腈的偶联反应，形成乙烯基碳二亚胺中间体，然后与炔烃串联环化，研究了多取代氨基吡啶的合成及荧光性质。进一步设计、合成和评价了带有叠氮基团的氨基吡啶作为潜在探针。它在 BSA 蛋白上的“点击-探测”实验表明了氨基吡啶作为生物探针支架的潜力。
