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.
- Department of Chemical Sciences - Reader - Complex Pathway Leader
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Blackburn, J., Molyneux, G., Pitard, A., Rice, C. R., Page, M. I., Afshinjavid, S., ... Hemming, K. (2016). Synthesis, conformation and antiproliferative activity of isothiazoloisoxazole 1,1-dioxides. Organic and Biomolecular Chemistry, 14(6), 2134-2144. https://doi.org/10.1039/C5OB02586A