Synthesis, conformation and antiproliferative activity of isothiazoloisoxazole 1,1-dioxides
J Blackburn1, G Molyneux1, A Pitard1
1Department of Chemical Sciences, School of Applied Sciences, University of Huddersfield, Huddersfield, HD1 3DH, UK. k.hemming@hud.ac.uk.
Abstract:
Sixteen new isothiazoloisoxazole 1,1-dioxides, one new isothiazolotriazole and one new isothiazolopyrazole have been synthesised by using 1,3-dipolar cycloadditions to isothiazole 1,1-dioxides. One sub-set of these isothiazoloisoxazoles showed low μM activity against a human breast carcinoma cell line, whilst a second sub-set plus the isothiazolotriazole demonstrated an interesting restricted rotation of sterically hindered bridgehead substituents. A thiazete 1,1-dioxide produced from one of the isothiazole 1,1-dioxides underwent conversion into an unknown 1,2,3-oxathiazolin-2-oxide upon treatment with Lewis acids, but was inert towards 1,3-dipoles and cyclopropenones. Six supporting crystal structures are included.
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