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Issue 10, 2013
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Continuous synthesis of pyridocarbazoles and initial photophysical and bioprobe characterization

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Abstract

Pyridocarbazoles when ligated to transition metals yield high affinity kinase inhibitors. While batch photocyclizations enable the synthesis of these heterocycles, the non-oxidative Mallory reaction only provides modest yields and difficult to purify mixtures. We demonstrate here that a flow-based Mallory cyclization provides superior results and enables observation of a clear isobestic point. The flow method allowed us to rapidly synthesize ten pyridocarbazoles and for the first time to document their interesting photophysical attributes. Preliminary characterization reveals that these molecules might be a new class of fluorescent bioprobe.

Graphical abstract: Continuous synthesis of pyridocarbazoles and initial photophysical and bioprobe characterization

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Publication details

The article was received on 01 Jul 2013, accepted on 30 Jul 2013 and first published on 31 Jul 2013


Article type: Edge Article
DOI: 10.1039/C3SC51846A
Citation: Chem. Sci., 2013,4, 4067-4070
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    Continuous synthesis of pyridocarbazoles and initial photophysical and bioprobe characterization

    D. T. McQuade, A. G. O'Brien, M. Dörr, R. Rajaratnam, U. Eisold, B. Monnanda, T. Nobuta, H. Löhmannsröben, E. Meggers and P. H. Seeberger, Chem. Sci., 2013, 4, 4067
    DOI: 10.1039/C3SC51846A

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