Synthesis and Fluorescent Properties of Aminopyridines and the Application in "Click and Probing"

Zongyang Li; Yaxuan Li; Wenxu Chang; Sen Pang; Xuefeng Li; Liusheng Duan; Zhenhua Zhang

doi:10.3390/molecules27051596

Synthesis and Fluorescent Properties of Aminopyridines and the Application in "Click and Probing"

Molecules. 2022 Feb 28;27(5):1596. doi: 10.3390/molecules27051596.

Authors

Zongyang Li^{1

2}, Yaxuan Li^{1

2}, Wenxu Chang^{1

2}, Sen Pang^{1

2}, Xuefeng Li^{1

2}, Liusheng Duan^{1

2}, Zhenhua Zhang^{1

2}

Affiliations

¹ College of Agronomy and Biotechnology, China Agricultural University, Beijing 100193, China.
² College of Science, China Agricultural University, Beijing 100193, China.

Abstract

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.

Keywords: aminopyridine; azide; click-and-probing; fluorescence.

Abstract

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