Expedient synthesis of an atypical oxazolidinone compound library.
In order to address the current downturn in the drug discovery pipeline, initiatives are being undertaken to synthesise screening libraries of sp3-rich, low molecular weight compounds. As part of the European Lead Factory initiative, the synthesis and derivatisation of a simple hexahydrooxazolo[5,4-c]pyridin-2(1H)-one bicyclic carbamate has been achieved. The synthetic route employed involved a telescoped hetero-Diels-Alder/[2,3]-sigmatropic rearrangement/cyclisation sequence to deliver the desired core scaffold containing two points for further diversification. When applied, this synthesis was found to be robust and scalable which allowed the production of a 155 compound library.
School of Chemistry, The University of Nottingham, University Park, Nottingham NG7 2RD, UK.
Sarah J
SJ
Cully
School of Chemistry, The University of Nottingham, University Park, Nottingham NG7 2RD, UK.
Thomas E
TE
Storr
School of Chemistry, The University of Nottingham, University Park, Nottingham NG7 2RD, UK.
Michael J
MJ
Rawling
School of Chemistry, University of East Anglia, Norwich NR4 7TJ, UK.
Induka R
IR
Abeysena
Sygnature Discovery, BioCity, Pennyfoot Street, Nottingham NG1 1GF, UK.
Daniel
D
Hamza
Sygnature Discovery, BioCity, Pennyfoot Street, Nottingham NG1 1GF, UK.
Geraint
G
Jones
Sygnature Discovery, BioCity, Pennyfoot Street, Nottingham NG1 1GF, UK.
Christopher A
CA
Pearce
Sygnature Discovery, BioCity, Pennyfoot Street, Nottingham NG1 1GF, UK.
Abdul
A
Quddus
X-ray Crystallography Section, School of Chemistry, The University of Nottingham, University Park, Nottingham NG7 2RD, UK.
William
W
Lewis
School of Chemistry, The University of Nottingham, University Park, Nottingham NG7 2RD, UK.
Robert A
RA
Stockman
D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D023303:Oxazolidinones / Q000138:chemical synthesis* / Q000737:chemistry; D054852:Small Molecule Libraries / Q000138:chemical synthesis* / Q000737:chemistry
D023303:Oxazolidinones; D054852:Small Molecule Libraries
Bicyclic; Library; Oxazolidinone; Scaffold; sp(3)-rich