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Org Lett. 2013 Sep 6;15(17):4312-5. doi: 10.1021/ol401705a. Epub 2013 Aug 12.

Synthesis and stability of oxetane analogs of thalidomide and lenalidomide.

Author information

1
Laboratorium für Organische Chemie, ETH Zürich, CH-8093 Zürich, Switzerland.

Abstract

Oxetanes are used in drug discovery to enable physicochemical and metabolic property enhancement for the structures to which they are grafted. An imide C═O to oxetane swap on thalidomide and lenalidomide templates provides analogs with similar physicochemical and in vitro properties of the parent drugs, with an important exception: oxetane analog 2 displays a clear differentiation with respect to human plasma stability. The prospect of limiting in vivo stability/metabolism, blocking in vivo racemization, and potentially altering teratogenicity is appealing.

PMID:
23937240
DOI:
10.1021/ol401705a
[Indexed for MEDLINE]

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