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 International Edition

DOI: 10.1002/anie.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: $5,510

Funder: European Research Council