Work

3‐Oxabicyclo[3.1.1]heptane as an Isostere of meta ‐Benzene

Year: 2025

Type: article

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%).

Source: Angewandte Chemie

DOI: 10.1002/ange.202505519

Authors: Dmitry Dibchak, Pavel K. Mykhailiuk

Institution: Enamine (Ukraine)

Language: English

Topic: Synthesis and biological activity

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $5,790

Funder: European Research Council