Cubanes in Medicinal Chemistry

Cubane is a highly strained saturated hydrocarbon system that has historically been of interest in theoretical organic chemistry. More recently it has become a molecule of interest for biological applications due to its inherent stability and limited toxicity. Of greater significance is the ability...

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Published inJournal of medicinal chemistry Vol. 62; no. 3; pp. 1078 - 1095
Main Authors Reekie, Tristan A, Williams, Craig M, Rendina, Louis M, Kassiou, Michael
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 14.02.2019
Subjects
Animals
Bridged-Ring Compounds - chemical synthesis
Bridged-Ring Compounds - pharmacology
Chemistry Techniques, Synthetic - methods
Chemistry, Pharmaceutical - methods
Cycloparaffins - chemical synthesis
Cycloparaffins - pharmacology
HEK293 Cells
Humans
Mice
Rats
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Summary:Cubane is a highly strained saturated hydrocarbon system that has historically been of interest in theoretical organic chemistry. More recently it has become a molecule of interest for biological applications due to its inherent stability and limited toxicity. Of greater significance is the ability to potentially functionalize cubane at each of its carbon atoms, providing complex biologically active molecules with unique spatial arrangements for probing active sites. These characteristics have led to an increased use of cubane in pharmaceutically relevant molecules. In this Perspective we describe synthetic methodology for accessing a range of functionalized cubanes and their applications in pharmaceuticals. We also provide some perspectives on challenges and future directions in the advancement of this field.
ISSN:0022-2623
1520-4804
DOI:10.1021/acs.jmedchem.8b00888