There is a widespread perception within the medicinal chemistry community that acetals and ketals and their nitrogen and sulfur homologues are unsuitable scaffolds for the design of orally delivered drugs due to an anticipation of instability under the acidic conditions of the stomach and upper gastrointestinal tract. However, the chemical stability of acetals, ketals and their nitrogen and sulfur homologues can readily be modulated by the judicious use of substituents that allows their application in circumstance that require either enhanced or diminished stability toward low pH. Moreover, acetals, ketals and aminals can combine conformational restriction with unique electronic-withdrawing properties that can lead to improved biological activity and pharmaceutical properties for a chemotype. This presentation will survey some of the applications of acetals, ketals and their sulfur and nitrogen homologues in the discovery of both orally bioavailable drugs or drug candidates and applications in drug delivery.

Geminal diheteroatomic motifs in drug design: Applications of acetals, ketals, and their sulfur and nitrogen homologues in medicinal chemistry

2019 Fall National Meeting

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