Hemming, Karl, Blackburn, Jack, Molyneux, Gary, Pitard, Arnaud, Rice, Craig R., Page, Michael I., Afshinjavid, S., Javid, Farideh A., Coles, Simon J. and Horton, Peter N. (2016) Synthesis, Conformation and Antiproliferative Activity of Isothiazoloisoxazole 1,1-dioxides. Organic and Biomolecular Chemistry, 14. pp. 2134-2144. ISSN 1477-0539
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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.
|Subjects:||Q Science > QD Chemistry|
|Schools:||School of Applied Sciences|
|Depositing User:||Karl Hemming|
|Date Deposited:||03 Feb 2016 14:51|
|Last Modified:||03 Feb 2016 14:55|
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