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Record W4394728589 · doi:10.1021/acs.jmedchem.3c02483

Development of Highly Potent and Selective Covalent FGFR4 Inhibitors Based on S <sub>N</sub> Ar Electrophiles

2024· article· en· W4394728589 on OpenAlexfundno aff
Moritz Schwarz, Maksym Kurkunov, Florian Wittlinger, Ramona Rudalska, Guiqun Wang, Martin P. Schwalm, Alexander Rasch, B.J. Wagner, Stefan Laufer, Stefan Knapp, Daniel Dauch, Matthias Gehringer

Bibliographic record

VenueJournal of Medicinal Chemistry · 2024
Typearticle
Languageen
FieldBiochemistry, Genetics and Molecular Biology
TopicFibroblast Growth Factor Research
Canadian institutionsnot available
FundersStructural Genomics ConsortiumJanssen PharmaceuticalsGenentechGenome CanadaBaden-Württemberg StiftungOntario Genomics InstituteDeutsche ForschungsgemeinschaftMerckBayerFonds der Chemischen IndustriePfizerDeutsches KrebsforschungszentrumTakeda Pharmaceutical CompanyBristol-Myers SquibbBoehringer Ingelheim
KeywordsChemistryElectrophileCovalent bondCombinatorial chemistryStereochemistryBiochemistryOrganic chemistry

Abstract

fetched live from OpenAlex

Fibroblast growth factor receptor 4 (FGFR4) is thought to be a driver in several cancer types, most notably in hepatocellular carcinoma. One way to achieve high potency and isoform selectivity for FGFR4 is covalently targeting a rare cysteine (C552) in the hinge region of its kinase domain that is not present in other FGFR family members (FGFR1–3). Typically, this cysteine is addressed via classical acrylamide electrophiles. We demonstrate that noncanonical covalent “warheads” based on nucleophilic aromatic substitution (S N Ar) chemistry can be employed in a rational manner to generate highly potent and (isoform-)selective FGFR4 inhibitors with a low intrinsic reactivity. Key compounds showed low to subnanomolar potency, efficient covalent inactivation kinetics, and excellent selectivity against the other FGFRs, the kinases with an equivalent cysteine, and a representative subset of the kinome. Moreover, these compounds achieved nanomolar potencies in cellular assays and demonstrated good microsomal stability, highlighting the potential of S N Ar-based approaches in covalent inhibitor design.

Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.

How this classification was reachedexpand

Full frame distilled prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.000
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesnone
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.005
Threshold uncertainty score0.585

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0000.000

Machine scores (provisional)

The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.

Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.

Opus teacher head0.007
GPT teacher head0.244
Teacher spread0.237 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it

Classification

machine, unvalidated

Machine predicted; a candidate call from one teacher head, not a consensus.

The models applied no category: nothing in the taxonomy fit this work.
Study designBench or experimental
Domainnot available
GenreEmpirical

How this classification was reached, model by model and score by score, is at the end of the page under "How this classification was reached".

Quick stats

Citations19
Published2024
Admission routes1
Has abstractyes

Explore more

Same venueJournal of Medicinal ChemistrySame topicFibroblast Growth Factor ResearchFrench-language works237,207