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

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 approac...

Full description

Saved in:
Bibliographic Details
Published inChemical science (Cambridge) Vol. 7; no. 4; pp. 264 - 2613
Main Authors Kutchukian, Peter S, Dropinski, James F, Dykstra, Kevin D, Li, Bing, DiRocco, Daniel A, Streckfuss, Eric C, Campeau, Louis-Charles, Cernak, Tim, Vachal, Petr, Davies, Ian W, Krska, Shane W, Dreher, Spencer D
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2016
Subjects
Chemical reactions
Chemistry
Chemistry, Multidisciplinary
Collection
Diagnostic systems
Evolution
Failure
Libraries
Physical Sciences
Principal component analysis
Science & Technology
Visualization
REACTION DISCOVERY
BORONIC ACIDS
CROSS-COUPLING REACTIONS
ROBUSTNESS SCREEN
HETEROCYCLIC CARBENE COMPLEXES
PALLADIUM PRECATALYST
RAPID ASSESSMENT
C-H BORYLATION
SUZUKI-MIYAURA
ARYL CHLORIDES
Online AccessGet full text

Cover

More Information
Summary: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. We report a standardized complex molecule diagnostic approach using collections of relevant drug-like molecules which we call chemistry informer libraries.
Bibliography:Electronic supplementary information (ESI) available. See DOI
10.1039/c5sc04751j
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:2041-6520
2041-6539
DOI:10.1039/c5sc04751j