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Molecules 2016, 21(9), 1230; doi:10.3390/molecules21091230

Combinatorial Synthesis of Structurally Diverse Triazole-Bridged Flavonoid Dimers and Trimers

1
Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK
2
Department of Biochemistry, University of Cambridge, Tennis Court Road, Cambridge CB2 1GA, UK
*
Author to whom correspondence should be addressed.
Academic Editor: Andrea Trabocchi
Received: 29 July 2016 / Revised: 26 August 2016 / Accepted: 8 September 2016 / Published: 16 September 2016
(This article belongs to the Special Issue Diversity Oriented Synthesis 2016)

Abstract

Flavonoids are a large family of compounds associated with a broad range of biologically useful properties. In recent years, synthetic compounds that contain two flavonoid units linked together have attracted attention in drug discovery and development projects. Numerous flavonoid dimer systems, incorporating a range of monomers attached via different linkers, have been reported to exhibit interesting bioactivities. From a medicinal chemistry perspective, the 1,2,3-triazole ring system has been identified as a particularly attractive linker moiety in dimeric derivatives (owing to several favourable attributes including proven biological relevance and metabolic stability) and triazole-bridged flavonoid dimers possessing anticancer and antimalarial activities have recently been reported. However, there are relatively few examples of libraries of triazole-bridged flavonoid dimers and the diversity of flavonoid subunits present within these is typically limited. Thus, this compound type arguably remains underexplored within drug discovery. Herein, we report a modular strategy for the synthesis of novel and biologically interesting triazole-bridged flavonoid heterodimers and also very rare heterotrimers from readily available starting materials. Application of this strategy has enabled step-efficient and systematic access to a library of structurally diverse compounds of this sort, with a variety of monomer units belonging to six different structural subclasses of flavonoid successfully incorporated. View Full-Text
Keywords: flavonoid; triazole; dimer; trimer; hybridization; structural diversity flavonoid; triazole; dimer; trimer; hybridization; structural diversity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Sum, T.H.; Sum, T.J.; Galloway, W.R.J.D.; Collins, S.; Twigg, D.G.; Hollfelder, F.; Spring, D.R. Combinatorial Synthesis of Structurally Diverse Triazole-Bridged Flavonoid Dimers and Trimers. Molecules 2016, 21, 1230.

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