What Rings Do Medicinal Chemists Use, And Why?
Poster Jan 24, 2017
M. D. Mackey
The vast majority of small molecule drugs contain at least one ring. The rigidity, synthetic accessibility and geometric preferences of rings mean that medicinal chemistry series are usually defined in terms of which ring or rings they have at their core. However, ring systems are more than just scaffolds waiting to be elaborated: the electrostatic and pharmacophoric properties of ring systems are usually crucial to the biological activity of the molecules that contain them.
We have conducted an investigation into the most common ring system and substitution patterns in the recent medicinal chemistry literature, as derived from the ChEMBL database. For each of these rings, the electrostatic potential has been calculated allowing the chemist to see at a glance the electronic properties of each system. In addition, applying the Spark bioisostere evaluation metric to the rings database reveals the best bioisosteric replacements for each ring system.
In the poster selected entries from the rings database are shown and discussed. The full data set is an invaluable aid to the medicinal chemist looking to understand the properties of their lead molecule and the opportunities for variation of its core.