Cubane Lore 

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Cubanes are a pretty neat class of molecules - in this video, we explore the applications of cubanes, and rank some impressive cubanes such as BUTTERCUBE!
Summary
In this, the host discusses Cubane, a cube-shaped molecule, and its potential applications in medicinal chemistry. Cubane is considered as a substitute for Benzene rings in new drug candidates. The 3D structure of Cubane allows for distinct interactions with target proteins or receptors. Additionally, Cubane can have different metabolites compared to Benzene. It is also explored in energetic materials. The video presents a tier list of various Cubane derivatives, highlighting their structures and uniqueness.
Highlights
💡 Cubane is a cube-shaped molecule that medicinal chemists want to use as a substitute for Benzene rings in new drug candidates.
💡 Substituting a Benzene ring with Cubane in an active pharmaceutical ingredient (API) could potentially improve binding to the target.
💡 Cubane's 3D structure allows for different interactions in space, unlike the flat Benzene ring.
💡 Cubane derivatives can have different metabolites compared to Benzene, which is important for drug elimination from the body.
💡 Cubane is also explored in energetic materials, although its large-scale production poses challenges.
💡 The tier list of Cubane derivatives ranks them based on their impressive structures, with S tier being the most impressive.
💡 The video acknowledges the need for more commercially available and affordable Cubane derivatives to advance research and drug development.
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Team
Writer/Producer - That Chemist (Joey)
Editor/Lead Animator - ReformLabs
3D Systems Engineer - Robot Chicken
Thumbnail Artist - RinFroggy
Acknowledgements
Thanks to the people on Twitter who helped suggest cubane references! Especially Kitspiroplatin for the reference of the extremely long tetracubane iodide! I also want to acknowledge that Tom will eventually make cubane.
References
Tom’s Cubane Series • Cubane Synthesis
Perfluorocubane • The First Real Life Pi...
Chemiolis Click Chem • Click Chemistry in Act...
Casual Chemistry Click Chem • Copper and Click Chemi...
Cubane Review Articles:
Cubanes in Med Chem doi.org/10.1021/acs.jmedchem.8...
Cubanes: 50 Years Later doi.org/10.1021/cr500523x
Bicubyl pubs.acs.org/doi/10.1021/ja98...
bidentate cubane ligand doi.org/10.1055/s-0029-1217083
butter cubane doi.org/10.1016/S0040-4039(00...
carboxycubane thioxanthylglycine - worldwide.espacenet.com/paten... (page 48)
cubane carboxylic acid doi.org/10.1002/chem.201901086
cubane dicarboxylic acid dimethyl ester doi.org/10.1055/s-0040-1705964
cubane doi.org/10.1055/s-1995-3961
cubene doi.org/10.1021/ja00229a057
cubyl phenyl ketone pubs.rsc.org/en/content/artic...
cubyl triflate pubs.acs.org/doi/abs/10.1021/...
cubylmethanol doi.org/10.1021/ol501750k
dideuterocubane pubs.acs.org/doi/10.1021/jp95...
diethynyl cubane pubs.acs.org/doi/abs/10.1021/...
diflucuburon doi.org/10.1002/anie.201510675
letepricube worldwide.espacenet.com/paten...
mercury cubane insanity doi.org/10.1021/cr500523x (compound 71)
methoxycarbonylcubane carboxylic acid - 10.1002/chem.201901086
octamethylcubane doi.org/10.1016/S0040-4039(00...
octacyclopropylcubane onlinelibrary.wiley.com/doi/a...
octanitrocubane doi.org/10.1002/(SICI)1521-37... (this DOI sucks)
octaphenylcubane pubs.acs.org/doi/abs/10.1021/...
perfluorocubane doi.org/10.1126/science.abq0516
perfluorooctamethylcubane pubs.acs.org/doi/abs/10.1021/...
tetracarbomethoxycubane link.springer.com/article/10....
tetrabromotetranitrocubane pubs.acs.org/doi/10.1021/jo97...
pedestal - doi.org/10.1002/anie.199214211
Molecules in this Tierlist
Bicubyl, bidentate cubane ligand, butter cubane, carboxycubane thioxanthylglycine, cubane carboxylic acid, cubane dicarboxylic acid dimethyl ester, cubane, cubene, cubyl phenyl ketone, cubyl triflate, cubylmethanol, dideuterocubane, diethynyl cubane, diflucuburon, letepricube, mercury cubane insanity, methoxycarbonylcubane carboxylic acid, octamethylcubane, octacyclopropylcubane, octanitrocubane, octaphenylcubane, perfluorocubane, perfluorooctamethylcubane, tetrabromotetranitrocubane, tetracarbomethoxycubane, tin cubane insanity, extremely long cubane, lead cubane insanity