Issue 4, 2016

Chemistry informer libraries: a chemoinformatics enabled approach to evaluate and advance synthetic methods

Abstract

Major new advances in synthetic chemistry methods are typically reported using simple, non-standardized reaction substrates, and reaction failures are rarely documented. This makes the evaluation and choice of a synthetic method difficult. We report a standardized complex molecule diagnostic approach using collections of relevant drug-like molecules which we call chemistry informer libraries. With this approach, all chemistry results, successes and failures, can be documented to compare and evolve synthetic methods. To aid in the visualization of chemistry results in drug-like physicochemical space we have used an informatics methodology termed principal component analysis. We have validated this method using palladium- and copper-catalyzed reactions, including Suzuki–Miyaura, cyanation and Buchwald–Hartwig amination.

Graphical abstract: Chemistry informer libraries: a chemoinformatics enabled approach to evaluate and advance synthetic methods

Supplementary files

Article information

Article type
Edge Article
Submitted
09 12 2015
Accepted
15 1 2016
First published
26 1 2016
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2016,7, 2604-2613

Author version available

Chemistry informer libraries: a chemoinformatics enabled approach to evaluate and advance synthetic methods

P. S. Kutchukian, J. F. Dropinski, K. D. Dykstra, B. Li, D. A. DiRocco, E. C. Streckfuss, L. Campeau, T. Cernak, P. Vachal, I. W. Davies, S. W. Krska and S. D. Dreher, Chem. Sci., 2016, 7, 2604 DOI: 10.1039/C5SC04751J

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