Format

Send to

Choose Destination
Chem Sci. 2016 Apr 21;7(4):2604-2613. doi: 10.1039/c5sc04751j. Epub 2016 Jan 26.

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

Author information

1
Department of Structural Chemistry , Merck Research Laboratories , Merck and Co., Inc. , Boston , MA 02115 , USA.
2
Department of Process and Analytical Chemistry , Merck Research Laboratories , Merck and Co., Inc. , Rahway , NJ 07065 , USA . Email: spencer_dreher@merck.com.
3
Department of Discovery Chemistry , Merck Research Laboratories , Merck and Co., Inc. , Rahway , NJ 07065 , USA . Email: shane_krska@merck.com.

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.

Supplemental Content

Full text links

Icon for Royal Society of Chemistry Icon for PubMed Central
Loading ...
Support Center