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3,3-Difluorooxetane – a Versatile Functional Group for Bioisosteric Replacements in Drug Discovery

14 August 2024, Version 1

Abstract

Functional group (FG) is one of the cornerstone concepts in organic chemistry and related areas. Wide spread of bioisosterism ideas in medicinal chemistry and beyond caused a striking rise in demand for novel FGs with defined impact on the developed compound properties. In this work, evaluation of 3,3-difluorooxetane unit (3,3-diFox) as a functional group for bioisosteric replacements is disclosed. Comprehensive experimental study (including multigram building block synthesis, quantification of steric and electronic properties, measurements of pKa, LogP, chemical stability, and biological evaluation of the 3,3-diFox-derived bioisostere of a drug candidate) revealed a prominent behavior of the 3,3-diFox fragment as a versatile substituent for early drug discovery programs.

Keywords

Fluorine
Oxetane
Building Blocks
Bioisosteres
Functional Groups

Supplementary materials

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Electronic supplementary materials containing experimental part, methods, protocols, copies of NMR spectra, and other details.
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Version History

Aug 14, 2024 Version 1

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The content is available under CC BY 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2024-c9p3f
D O I: 10.26434/chemrxiv-2024-c9p3f [opens in a new tab]

Funding

Enamine

Author’s competing interest statement

Most of the authors are / have been employees, trainees, or consulting scientists of Enamine Ltd. that offers all the building blocks described in this paper in the company’s catalog.

Ethics

The author(s) declare that they have sought and gained approval from the relevant ethics committee/IRB for this research and its publication.

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