Organic Letters
Organic Letters
4 years ago

Rapid Access to a Broad Range of 6′-Substituted Firefly Luciferin Analogues Reveals Surprising Emitters and Inhibitors

Rapid Access to a Broad Range of 6′-Substituted Firefly Luciferin Analogues Reveals Surprising Emitters and Inhibitors
Kate L. Liebmann, Spencer T. Adams, Deepak K. Sharma, Stephen C. Miller
Light-emitting firefly luciferin analogues contain electron-donating groups in the 6′-position, but the scope of known 6′-substitution remains narrow. A two-step route to a broad range of 6′-substituted luciferin analogues was developed to fill this void and enable more extensive study of the 6′-functionality. This chemistry allowed direct access to “caged” amide and bright azetidine analogues, but also revealed thioether inhibitors and unexpectedly luminogenic aryl amine derivatives.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02806

DOI: 10.1021/acs.orglett.7b02806

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