We present a comprehensive update on the concept of privileged structures in medicinal chemistry. The term “privileged scaffold” was coined in 1988 when it was discovered that benzodiazepine derivatives serve as effective ligands for a variety of different receptors even from different classes. Current medicinal chemistry efforts seem to pursue rivaling concepts of using privileged structures <i>vs</i>. performing rare chemistry to yield new scaffolds. We have analyzed the scaffolds of bioactive compounds annotated in ChEMBL. We obtained information on the macromolecular targets of both frequently used and underexplored scaffolds and studied their expected target promiscuity. We also attempt to provide an answer to the question whether performing unusual chemistry could deliver new target-selective scaffolds.

Old and new privileged scaffolds for medicinal chemistry

253rd National Meeting (2017)

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