Issue 87, 2015
From the journal:

RSC Advances

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†

Ajay Kanungo,‡a   Dipendu Patra,‡a   Sanghamitra Mukherjee,a   Tridib Mahata,a   Prakas R. Maulika  and  Sanjay Dutta*a  

* Corresponding authors

a Organic & Medicinal Chemistry Division, CSIR-Indian Institute of Chemical Biology, 4, Raja S. C. Mullick Road, Jadavpur, Kolkata 700 032, India
E-mail: sanjaydutta@iicb.res.in
Fax: +91-33-2473-5197

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

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Article information

DOI
https://doi.org/10.1039/C5RA12960E
Article type
Paper
Submitted
03 Jul 2015
Accepted
11 Aug 2015
First published
19 Aug 2015

RSC Adv., 2015,5, 70958-70967

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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

A. Kanungo, D. Patra, S. Mukherjee, T. Mahata, P. R. Maulik and S. Dutta, RSC Adv., 2015, 5, 70958 DOI: 10.1039/C5RA12960E

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