3‐Oxabicyclo[3.1.1]heptane as an Isostere of <i>meta</i> ‐Benzene
3-Oxabicyclo[3.1.1]heptanes were designed as saturated isosteres of meta-benzene. Crystallographic analysis revealed that these structures and meta-benzene have identical geometric properties. Replacement of the central benzene ring in the anticancer drug Sonidegib with 3-oxabicyclo[3.1.1]heptane provided a patent-free analogue with a nanomolar potency, reduced lipophilicity, and improved water solubility (>500%).
Authors
- Pavel K. Mykhailiuk (ORCID: https://orcid.org/0000-0003-1821-9011)
- Dmitry Dibchak
Institutions
- Enamine (Ukraine) (UA)
Publication Details
- Journal
- Angewandte Chemie International Edition
- Published
- 2025-03-28
- DOI
- https://doi.org/10.1002/anie.202505519
- Citations
- 14
- Primary Topic
- Asymmetric Hydrogenation and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 7.52