ArticleACS medicinal chemistry letters2013
Metabolically Stable tert-Butyl Replacement.
Article in ACS medicinal chemistry letters, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 33 papers.
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Who cites it
33 citing papers in PubMed.
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- Synthesis and SAR Studies of Acyl-Thiourea Platinum(II) Complexes Yield Analogs with Dual-Stage Antiplasmodium Activity.ACS medicinal chemistry letters · 2025Article
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- Aryl (β,β',β″-Trifluoro)-Organic letters · 2023Article
- Alkyl sulfinates as cross-coupling partners for programmable and stereospecific installation of C(spNature chemistry · 2023Article
- Deoxytrifluoromethylation of Alcohols.Journal of the American Chemical Society · 2022Article
- Put a ring on it: application of small aliphatic rings in medicinal chemistry.RSC medicinal chemistry · 2021Review
- Strategies for the expression and characterization of artificial myoglobin-based carbene transferases.Methods in enzymology · 2020Article
- Discovery and Optimization of Salicylic Acid-Derived Sulfonamide Inhibitors of the WD Repeat-Containing Protein 5-MYC Protein-Protein Interaction.Journal of medicinal chemistry · 2019Article
Corrections and comments
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Authors and funding
9 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Susceptibility to metabolism is a common issue with the tert-butyl group on compounds of medicinal interest. We demonstrate an approach of removing all the fully sp(3) C-Hs from a tert-butyl group: replacing some C-Hs with C-Fs and increasing the s-character of the remaining C-Hs. This approach gave a trifluoromethylcyclopropyl group, which increased metabolic stability. Trifluoromethylcyclopropyl-containing analogues had consistently higher metabolic stability in vitro and in vivo compared to their tert-butyl-containing counterparts.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.