Carbonyl substitutes

07 June 2008 - Drug discovery

SpiroCycliOxetanesWuitschik2008  When 15 people get together writing a single 4 page article something must be going on (DOI). Researchers from Hoffmann-La Roche and ETH Zurich have noted the chemical similarities between carbonyl groups and oxetane groups. This is useful information: in drug discovery carbonyl groups are often too reactive while hydrogen bonding properties are similar and larger molecular volume of oxetanes may be an advantage. The researchers examined properties such as distribution coefficient, solubility and pKa for a large number of amines fitted with a carbonyl, oxetane or geminal dimethyl group. The latter group matches the carbonyl group in molecular volume

The idea is not entirely new: the same researchers already arrived at a similar conclusion in 2006 with a different set of amino oxetanes (DOI).