Development of New Fluorescent Xanthines as Kinase Inhibitors
- 25 February 2010
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 12 (6), 1212-1215
- https://doi.org/10.1021/ol100011n
Abstract
An efficient and versatile synthetic approach for the preparation of highly substituted xanthine derivatives has been developed by a combination of direct N7- and C8-arylation. With this method, diverse xanthine analogues were prepared and potent kinase inhibitors could be identified. For example, compound 8a inhibits PI3Ks and proliferation in T47D tumor cells. In addition, these xanthine-based kinase inhibitors exhibited significant fluorescence emission in a concentration-dependent response.Keywords
This publication has 50 references indexed in Scilit:
- Copper‐Catalyzed Direct C Arylation of Heterocycles with Aryl Bromides: Discovery of Fluorescent Core FrameworksAngewandte Chemie-International Edition, 2009
- Synthesis of 6,8,9-Tri- and 2,6,8,9-Tetrasubstituted Purines by a Combination of the Suzuki Cross-coupling, N-Arylation, and Direct C−H Arylation ReactionsThe Journal of Organic Chemistry, 2008
- Synthesis of 2‐Arylbenzoxazoles by Copper‐Catalyzed Intramolecular Oxidative C-O Coupling of BenzanilidesAngewandte Chemie-International Edition, 2008
- Direct Functionalization of Nitrogen Heterocycles via Rh-Catalyzed C−H Bond ActivationAccounts of Chemical Research, 2008
- Direct transition metal-catalyzed functionalization of heteroaromatic compoundsChemical Society Reviews, 2007
- Interstrand Cross-Links Generated by Abasic Sites in Duplex DNAJournal of the American Chemical Society, 2007
- A dual PI3 kinase/mTOR inhibitor reveals emergent efficacy in gliomaCancer Cell, 2006
- High Frequency of Mutations of the PIK3CA Gene in Human CancersScience, 2004
- Development of novel cell-permeable DNA sensitive dyes using combinatorial synthesis and cell-based screeningElectronic supplementary information (ESI) available: experimental section. See http://www.rsc.org/suppdata/cc/b3/b303960a/Chemical Communications, 2003
- The Phosphoinositide 3-Kinase PathwayScience, 2002