Partially Saturated Bicyclic Heteroaromatics as an sp³-Enriched Fragment Collection.
Angewandte Chemie International Edition
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Twigg, D., Kondo, N., Mitchell, S., Galloway, W., Sore, H., Madin, A., & Spring, D. (2016). Partially Saturated Bicyclic Heteroaromatics as an sp³-Enriched Fragment Collection.. Angewandte Chemie International Edition, 55 (40), 12479-12483. https://doi.org/10.1002/anie.201606496
Fragment-based lead generation has proven to be an effective means of identifying high-quality lead compounds for drug discovery programs. However, the fragment screening sets often used are principally comprised of sp²-rich aromatic compounds, which limits the structural (and hence biological) diversity of the library. Herein, we describe strategies for the synthesis of a series of partially saturated bicyclic heteroaromatic scaffolds with enhanced sp³ character. Subsequent derivatization led to a fragment collection featuring regio- and stereo-controlled introduction of substituents on the saturated ring system, often with formation of new stereocenters.
drug design, drug discovery, fused-ring systems, nitrogen heterocycles, synthetic methods
Is supplemented by: https://doi.org/10.1002/anie.201606496
EPSRC BBSRC MRC Wellcome Trust D.G.T. thanks AstraZeneca for funding. S.L.M. thanks BASF for funding. .
European Research Council (279337)
Royal Society (WM150022)
External DOI: https://doi.org/10.1002/anie.201606496
This record's URL: https://www.repository.cam.ac.uk/handle/1810/260773