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Regioselective sulfamoylation at low temperature enables concise syntheses of putative small molecule inhibitors of sulfatases

Lookup NU author(s): Duncan MillerORCiD, Dr Benoit Carbain, Dr Gary Beale, Dr Sari Alhasan, Professor Helen ReevesORCiD, Dr Ulrich Baisch, Professor Herbie Newell, Emeritus Professor Bernard Golding, Professor Roger Griffin

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Abstract

Regioselective sulfamoylation of primary hydroxyl groups enabled a 5-step synthesis (overall yield 17%) of the first reported small molecule inhibitor of sulfatase-1 and 2, ((2S, 3R, 4R, 5S, 6R)-4,5-dihydroxy-2-methoxy-6-((sulfamoyloxy)methyl) tetrahydro-2H-pyran-3-yl) sulfamic acid, which obviated the use of hydroxyl protecting groups and is a marked improvement on the reported 9-step synthesis (overall yield 9%) employing hazardous trifluoromethylsulfonyl azide. The sulfamoylation methodology was used to prepare a range of derivatives of 1, and inhibition data was generated for Sulf-2, ARSA and ARSB.

Publication metadata

Author(s): Miller DC, Carbain B, Beale GS, Alhasan SF, Reeves HL, Baisch U, Newell DR, Golding BT, Griffin RJ

Publication type: Article

Publication status: Published

Journal: Organic & Biomolecular Chemistry

Year: 2015

Volume: 13

Issue: 18

Pages: 5279-5284

Print publication date: 14/05/2015

Online publication date: 31/03/2015

Acceptance date: 31/03/2015

Date deposited: 15/12/2015

ISSN (print): 1477-0520

ISSN (electronic): 1477-0539

Publisher: Royal Society of Chemistry

URL: http://dx.doi.org/10.1039/c5ob00211g

DOI: 10.1039/c5ob00211g

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