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Investigating 3,3-diaryloxetanes as potential bioisosteres through matched molecular pair analysisElectronic supplementary information (ESI) available: Spectroscopic data of synthesized compounds, and experimental procedures for ADME data, and table of log Ddata. See DOI: 10.1039/d1md00248a
- Source :
- MedChemComm; 2021, Vol. 12 Issue: 12 p2045-2052, 8p
- Publication Year :
- 2021
-
Abstract
- Oxetanes have received increasing interest in medicinal chemistry as attractive polar and low molecular weight motifs. The application of oxetanes as replacements for methylene, methyl, gem-dimethyl and carbonyl groups has been demonstrated to often improve chemical properties of target molecules for drug discovery purposes. The investigation of the properties of 3,3-diaryloxetanes, particularly of interest as a benzophenone replacement, remains largely unexplored. With recent synthetic advances in accessing this motif we studied the effects of 3,3-diaryloxetanes on the physicochemical properties of ‘drug-like’ molecules. Here, we describe our efforts in the design and synthesis of a range of drug-like compounds for matched molecular pair analysis to investigate the viability of the 3,3-diaryloxetane motif as a replacement group in drug discovery. We conclude that the properties of the diaryloxetanes and ketones are similar, and generally superior to related alkyl linkers, and that diaryloxetanes provide a potentially useful new design element.
Details
- Language :
- English
- ISSN :
- 20402503 and 20402511
- Volume :
- 12
- Issue :
- 12
- Database :
- Supplemental Index
- Journal :
- MedChemComm
- Publication Type :
- Periodical
- Accession number :
- ejs58483253
- Full Text :
- https://doi.org/10.1039/d1md00248a