Put a ring on it: application of small aliphatic rings in medicinal chemistry

Literature Information

Publication Date 2021-01-07
DOI 10.1039/D0MD00370K
Impact Factor 0
Authors

Matthias R. Bauer, Paolo Di Fruscia, Simon C. C. Lucas, Iacovos N. Michaelides, Jennifer E. Nelson, R. Ian Storer, Benjamin C. Whitehurst


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Abstract

Aliphatic three- and four-membered rings including cyclopropanes, cyclobutanes, oxetanes, azetidines and bicyclo[1.1.1]pentanes have been increasingly exploited in medicinal chemistry for their beneficial physicochemical properties and applications as functional group bioisosteres. This review provides a historical perspective and comparative up to date overview of commonly applied small rings, exemplifying key principles with recent literature examples. In addition to describing the merits and advantages of each ring system, potential hazards and liabilities are also illustrated and explained, including any significant chemical or metabolic stability and toxicity risks.

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