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Continuous synthesis of pyridocarbazoles and initial photophysical and bioprobe characterization

  • 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.

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Author:D. Tyler McQuade, Alexander G. O'Brien, Markus Dörr, Rajathees Rajaratnam, Ursula EisoldORCiDGND, Bopanna Monnanda, Tomoya Nobuta, Hans-Gerd LöhmannsröbenGND, Eric Meggers, Peter H. Seeberger
Series (Serial Number):Postprints der Universität Potsdam : Mathematisch-Naturwissenschaftliche Reihe (246)
Document Type:Postprint
Date of first Publication:2013/07/31
Year of Completion:2013
Publishing Institution:Universität Potsdam
Release Date:2016/09/06
Tag:complexes; continuous-flow; efficient; light; phenanthrenes; photochemical synthesis; protein-kinase inhibitors
First Page:4067
Last Page:4070
Source:Chem. Sci. (2013) Nr. 4, S. 4067-4070. - DOI: 10.1039/C3SC51846A
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Peer Review:Referiert
Publication Way:Open Access
Licence (German):License LogoKeine Nutzungslizenz vergeben - es gilt das deutsche Urheberrecht