ArticleACS medicinal chemistry letters2020
Stereochemical Differences in Fluorocyclopropyl Amides Enable Tuning of Btk Inhibition and Off-Target Activity.
Article in ACS medicinal chemistry letters, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed, 16 citations in OpenAlex.
- Unique fluoroalkyl substituents: is there life after CFChemical science · 2026Review
- Discovery of novel acridine based inhibitors of Bruton's tyrosine kinase (BTK) via pharmacophore modeling and machine learning-driven virtual screening followed by molecular dynamic studies.Journal of computer-aided molecular design · 2026Article
- Article
- Structural Complementarity of Bruton's Tyrosine Kinase and Its Inhibitors for Implication in B-Cell Malignancies and Autoimmune Diseases.Pharmaceuticals (Basel, Switzerland) · 2023Review
- When Cofactors Aren't X Factors: Functional Groups That Are Labile in Human Liver Microsomes in the Absence of NADPH.ACS medicinal chemistry letters · 2022Article
- The Development of BTK Inhibitors: A Five-Year Update.Molecules (Basel, Switzerland) · 2021Review
- Heteroelement Analogues of Benzoxaborole and Related Ring Expanded Systems.Molecules (Basel, Switzerland) · 2021Review
- Put a ring on it: application of small aliphatic rings in medicinal chemistry.RSC medicinal chemistry · 2021Review
- Novel Approach to the Synthesis of 3-amino-4-arylpyridin-2(1Chemistry of heterocyclic compounds · 2021Article
Corrections and comments
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Authors and funding
19 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Bruton's tyrosine kinase (Btk) is thought to play a pathogenic role in chronic immune diseases such as rheumatoid arthritis and lupus. While covalent, irreversible Btk inhibitors are approved for treatment of hematologic malignancies, they are not approved for autoimmune indications. In efforts to develop additional series of reversible Btk inhibitors for chronic immune diseases, we sought to differentiate from our clinical stage inhibitor fenebrutinib using cyclopropyl amide isosteres of the 2-aminopyridyl group to occupy the flat, lipophilic H2 pocket. While drug-like properties were retained-and in some cases improved-a safety liability in the form of hERG inhibition was observed. When a fluorocyclopropyl amide was incorporated, Btk and off-target activity was found to be stereodependent and a lead compound was identified in the form of the (
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Registered trials
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