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...

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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
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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. We report a standardized complex molecule diagnostic approach using collections of relevant drug-like molecules which we call chemistry informer libraries.
AbstractList 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.
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.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.
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.
Author Campeau, Louis-Charles
Cernak, Tim
DiRocco, Daniel A
Streckfuss, Eric C
Dreher, Spencer D
Davies, Ian W
Dykstra, Kevin D
Vachal, Petr
Kutchukian, Peter S
Li, Bing
Dropinski, James F
Krska, Shane W
AuthorAffiliation Department of Process and Analytical Chemistry
Department of Discovery Chemistry
Merck Research Laboratories
Department of Structural Chemistry
Merck and Co., Inc
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  givenname: Peter S
  surname: Kutchukian
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  surname: Dropinski
  fullname: Dropinski, James F
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  fullname: Krska, Shane W
– sequence: 12
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BackLink https://www.ncbi.nlm.nih.gov/pubmed/28660032$$D View this record in MEDLINE/PubMed
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Issue 4
Keywords REACTION DISCOVERY
BORONIC ACIDS
CROSS-COUPLING REACTIONS
ROBUSTNESS SCREEN
HETEROCYCLIC CARBENE COMPLEXES
PALLADIUM PRECATALYST
RAPID ASSESSMENT
C-H BORYLATION
SUZUKI-MIYAURA
ARYL CHLORIDES
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Snippet Major new advances in synthetic chemistry methods are typically reported using simple, non-standardized reaction substrates, and reaction failures are rarely...
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SubjectTerms Chemical reactions
Chemistry
Chemistry, Multidisciplinary
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Evolution
Failure
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Physical Sciences
Principal component analysis
Science & Technology
Visualization
Title Chemistry informer libraries: a chemoinformatics enabled approach to evaluate and advance synthetic methods
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