Synthesis of azetidine-based beta-amino alcohols

Linda Supe

doi:10.3390/ECMC2022-13471

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Synthesis of azetidine-based beta-amino alcohols

Linda Supe

¹ Latvian Institute of Organic Synthesis

Academic Editor: Alfredo Berzal-Herranz

Published: 01 November 2022 by MDPI in 8th International Electronic Conference on Medicinal Chemistry session Small molecules as drug candidates

https://doi.org/10.3390/ECMC2022-13471

Abstract:

Beta-amino alcohols are versatile chemicals used as scaffolds in medicinal chemistry and are key factors for the efficacy of numerous pharmaceutical products. Locking the conformation of the active fragment in bioactive molecules may increase the potency and selectivity towards target receptor. Small rings especially the azetidine framework can serve as conformational lock yet providing the necessary size for receptor binding. Herein we report the synthesis of enantiopure beta-amino alcohols where the motif is combined with a structurally constrained azetidine cycle. The key steps towards target molecules include base-induced azetidine ring closure and subsequent beta-amino alcohol core installation.

Acknowledgements The research was funded by ERDF (Grant No. 1.1.1.2/VIAA/4/20/755)

Keywords: beta-amino alcohols; 2,4-azetidines; 2,2,4-azetidines; asymmetric synthesis

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Linda Supe