3‐Oxabicyclo[3.1.1]heptane as an Isostere of <i>meta</i> ‐Benzene

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 (&gt;500%).

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Publication Details

Journal
Angewandte Chemie
Published
2025-03-28
DOI
https://doi.org/10.1002/ange.202505519
Citations
1
Primary Topic
Catalysis and Oxidation Reactions
Type
article
Field-Weighted Citation Impact
0.39
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article

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

Pavel K. Mykhailiuk, Dmitry Dibchak
1 citations
Angewandte Chemie
Catalysis and Oxidation Reactions
0.39
article

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

Pavel K. Mykhailiuk, Dmitry Dibchak
article en
1 citations

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 (&gt;500%).

Angewandte ChemieVol. 137(25)
Enamine (Ukraine) (UA)
Openalex Percentile: Top 46%
Catalysis and Oxidation Reactions
0.39
DOIOpen Access PDFOpenAlex
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3‐Oxabicyclo[3.1.1]heptane as an Isostere of <i>meta</i> ‐Benzene — Pavel K. Mykhailiuk, Dmitry Dibchak · Angewandte Chemie (2025) | TGRS Research Map | TGRS