Densely functionalised spirocyclic oxetane-piperidine scaffolds for drug discovery

Gemma C Geary; Andrew Nortcliffe; Christopher A Pearce; Daniel Hamza; Geraint Jones; Christopher J Moody

doi:10.1016/j.bmc.2017.12.012

Densely functionalised spirocyclic oxetane-piperidine scaffolds for drug discovery

Bioorg Med Chem. 2018 Feb 15;26(4):791-797. doi: 10.1016/j.bmc.2017.12.012. Epub 2017 Dec 8.

Authors

Gemma C Geary¹, Andrew Nortcliffe¹, Christopher A Pearce², Daniel Hamza², Geraint Jones², Christopher J Moody³

Affiliations

¹ School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UK.
² Sygnature Discovery Ltd, BioCity, Pennyfoot Street, Nottingham NG1 1GF, UK.
³ School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UK. Electronic address: c.j.moody@nottingham.ac.uk.

PMID: 29366687
DOI: 10.1016/j.bmc.2017.12.012

Abstract

A spirocyclic, sp³-atom rich oxetane-containing scaffold was synthesised in just two steps via a gold catalysed propargylic alcohol rearrangement. The key gold cyclisation can be undertaken on a 40 g scale allowing the preparation of 419 lead-like compounds based on the scaffold for the European Lead Factory.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Cyclization
Drug Design*
Ethers, Cyclic / chemistry*
Gold / chemistry
Piperidines / chemistry*
Small Molecule Libraries / chemical synthesis
Small Molecule Libraries / chemistry*

Substances

Ethers, Cyclic
Piperidines
Small Molecule Libraries
piperidine
Gold
oxetane