Synthesis of a visibly emissive 9-nitro-2,3-dihydro-1H-pyrimido[1,2-a]quinoxalin-5-amine scaffold with large stokes shift and live cell imaging?
RSC Advances Pub Date: 2015-08-19 DOI: 10.1039/C5RA12960E
Abstract
We have developed a novel fluorescent scaffold 4 which is a 9-nitro-2,3-dihydro-1H-pyrimido[1,2-a]quinoxalin-5-amine derivative from the reaction between di-tert-butyl but-2-ynedioate and a quinoxaline molecule containing a dimethyl amine side tail in high yield. The synthesis of scaffold 4 involves an sp3 C–N bond cleavage mechanism which is not very common. The scaffolds 4 is emissive in the visible range λem ～ (517–540) nm with large stokes shifts (5005–6378) cm?1 in ethanol. Laser confocal microscopy of the live HepG2 cells treated with compound 4f shows that it can be used for live cell imaging in nanomolar concentrations.
![Graphical abstract: Synthesis of a visibly emissive 9-nitro-2,3-dihydro-1H-pyrimido[1,2-a]quinoxalin-5-amine scaffold with large stokes shift and live cell imaging](http://scimg.chem960.com/usr/1/C5RA12960E.jpg)
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Journal Name：RSC Advances
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