Heterocyclic Regioisomer Enumeration (HREMS): A Cheminformatics Design Tool

We
report the development and implementation of a cheminformatics
tool which aids in the design of compounds during exploratory chemistry
and lead optimization. The Heterocyclic Regioisomer Enumeration and
MDDR Search (HREMS) tool allows medicinal chemists to build greater
structural diversity into their synthetic planning by enabling a systematic,
automated enumeration of heterocyclic regioisomers of target structures.
To help chemists overcome biases arising from past experience or synthetic
accessibility, the HREMS tool further provides statistics on clinical
testing for each enumerated regioisomer substructure using an automated
search of a commercial database. Ready access to this type of information
can help chemists make informed choices on the targets they will pursue
being mindful of past experience with these structures in drug development.
This tool and its components can be incorporated into other cheminformatics
workflows to leverage their capabilities in triaging and in silico
compound enumeration.