Oxetanes as Promising Modules in Drug Discovery

Ring the changes: Introduction of an oxetane ring results in remarkably improved physico‐ and biochemical properties of the underlying scaffold. The oxetane ring confers enhanced solubility, reduces the metabolic degredation, lipophilicity, and amphiphilicity, and modulates the basicity of a nearby...

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Published inAngewandte Chemie International Edition Vol. 45; no. 46; pp. 7736 - 7739
Main Authors Wuitschik, Georg, Rogers-Evans, Mark, Müller, Klaus, Fischer, Holger, Wagner, Björn, Schuler, Franz, Polonchuk, Liudmila, Carreira, Erick M.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 27.11.2006
WILEY‐VCH Verlag
Wiley
Subjects
Animals
Biotransformation - drug effects
Chemistry
Chemistry, Multidisciplinary
Drug Design
Drug Stability
Ethers, Cyclic - chemistry
Ethers, Cyclic - metabolism
Ethers, Cyclic - pharmacology
Humans
metabolism
Mice
Microsomes - drug effects
Microsomes - metabolism
Molecular Structure
oxetanes
Physical Sciences
Science & Technology
small ring systems
synthesis design
drug design
PARTIAL MOLAR VOLUMES
small ring systems
RING
metabolism
oxetanes
synthesis design
WATER
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Summary:Ring the changes: Introduction of an oxetane ring results in remarkably improved physico‐ and biochemical properties of the underlying scaffold. The oxetane ring confers enhanced solubility, reduces the metabolic degredation, lipophilicity, and amphiphilicity, and modulates the basicity of a nearby amine group.
Bibliography:ArticleID:ANIE200602343
We thank the Swiss National Science Foundation and F. Hoffmann-La Roche AG for support of this research. We are very indebted to I. Parrilla, F. Senner, and P. Warga for their great dedication in measuring important physicochemical data described in this work.
F. Hoffmann-La Roche AG
ark:/67375/WNG-4D2R68R9-9
Swiss National Science Foundation
istex:4EE75E54575B75B33376F5C89FB670752190DEA6
We thank the Swiss National Science Foundation and F. Hoffmann–La Roche AG for support of this research. We are very indebted to I. Parrilla, F. Senner, and P. Warga for their great dedication in measuring important physicochemical data described in this work.
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200602343