3‐Oxabicyclo[3.1.1]heptane as an Isostere of <i>meta</i> ‐Benzene
D
Dmitry Dibchak
(Enamine Ltd. Winston Churchill st. 78 Kyiv 02094 Ukraine)
P
Pavel K. Mykhailiuk
(Enamine Ltd, Winston Churchill St. 78, 02094 Kyiv, Ukraine)
Abstract
Abstract 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%).
Article Details
Volume / Issue
Vol. 64, Issue 25
Published
June 17, 2025
ISSN
1433-7851
Publisher
Wiley
Authors (2)
D
Dmitry Dibchak
Enamine Ltd. Winston Churchill st. 78 Kyiv 02094 Ukraine
P
Pavel K. Mykhailiuk
Enamine Ltd, Winston Churchill St. 78, 02094 Kyiv, Ukraine
Related Articles from this Journal
Extending Chain Length of PNP Pincer Ligands Triggers Catalytic Activity of Gold–Copper Nanoclusters in Aerobic Oxidations
Ying Zhang, Chao Ge et al.
Aug 2026
10.1002/anie.3126258
Downsizing the Histone H3–H4 Quaternary Structure Into Foldamer Mimetics Yields High‐Affinity and Cell‐Permeable Ligands of ASF1
Bo Li, Marie E. Perrin et al.
Aug 2026
10.1002/anie.4112426
Step‐Associated Cu‐Ceria Interfaces Enhance Catalytic Activity and Selectivity
Shuxuan Feng, Shan Jiang et al.
Aug 2026
10.1002/anie.5628406
Gold Clusters With Open‐Shell Ligands: Superatom Mediated Magnetic Interaction
Katsuya Mutoh, Kosei Hayashi et al.
Aug 2026
10.1002/anie.3543072
Oxophilic Gallium Single‐Atom Regulating Micropore‐Confined Os Atomic Clusters Enables Efficient Alkaline Hydrogen Electrocatalysis
Mengyang Yang, Ling Li et al.
Aug 2026
10.1002/anie.2044894